JP2008505122A - ガススパージングを用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 - Google Patents
ガススパージングを用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 Download PDFInfo
- Publication number
- JP2008505122A JP2008505122A JP2007519536A JP2007519536A JP2008505122A JP 2008505122 A JP2008505122 A JP 2008505122A JP 2007519536 A JP2007519536 A JP 2007519536A JP 2007519536 A JP2007519536 A JP 2007519536A JP 2008505122 A JP2008505122 A JP 2008505122A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- mixture
- aldaric
- salt
- aldonic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000015572 biosynthetic process Effects 0.000 title description 5
- 238000003786 synthesis reaction Methods 0.000 title description 4
- 239000002253 acid Substances 0.000 claims abstract description 144
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000002596 lactones Chemical class 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 25
- 150000007513 acids Chemical class 0.000 claims description 24
- 239000011877 solvent mixture Substances 0.000 claims description 21
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 20
- 239000003125 aqueous solvent Substances 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 239000007858 starting material Substances 0.000 claims description 16
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 claims description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 12
- 235000012208 gluconic acid Nutrition 0.000 claims description 11
- QXKAIJAYHKCRRA-UHFFFAOYSA-N D-lyxonic acid Natural products OCC(O)C(O)C(O)C(O)=O QXKAIJAYHKCRRA-UHFFFAOYSA-N 0.000 claims description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000000174 gluconic acid Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000011065 in-situ storage Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- RGHNJXZEOKUKBD-MGCNEYSASA-N D-galactonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-MGCNEYSASA-N 0.000 claims description 5
- QXKAIJAYHKCRRA-UZBSEBFBSA-N D-lyxonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-UZBSEBFBSA-N 0.000 claims description 5
- RGHNJXZEOKUKBD-MBMOQRBOSA-N D-mannonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-MBMOQRBOSA-N 0.000 claims description 5
- QXKAIJAYHKCRRA-FLRLBIABSA-N D-xylonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)C(O)=O QXKAIJAYHKCRRA-FLRLBIABSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 claims description 5
- RGHNJXZEOKUKBD-SKNVOMKLSA-N L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SKNVOMKLSA-N 0.000 claims description 5
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- RGHNJXZEOKUKBD-AIHAYLRMSA-N D-altronic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-AIHAYLRMSA-N 0.000 claims description 4
- QXKAIJAYHKCRRA-JJYYJPOSSA-N D-arabinonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-JJYYJPOSSA-N 0.000 claims description 4
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 claims description 4
- OIYFAQRHWMVENL-UHFFFAOYSA-N 2-(4-oxopyran-3-yl)acetic acid Chemical compound OC(=O)CC1=COC=CC1=O OIYFAQRHWMVENL-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 159000000007 calcium salts Chemical class 0.000 claims description 3
- 239000003729 cation exchange resin Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 159000000000 sodium salts Chemical group 0.000 claims description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 229940095625 calcium glucarate Drugs 0.000 claims 1
- UGZVNIRNPPEDHM-SBBOJQDXSA-L calcium;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxyhexanedioate Chemical group [Ca+2].[O-]C(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O UGZVNIRNPPEDHM-SBBOJQDXSA-L 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 239000000047 product Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 15
- 229950006191 gluconic acid Drugs 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- -1 aldose carbohydrates Chemical class 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 238000013019 agitation Methods 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- RGHNJXZEOKUKBD-QMKXCQHVSA-N (2r,3r,4s,5s)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-QMKXCQHVSA-N 0.000 description 3
- QRFNDAVXJCGLFB-GJPGBQJBSA-N (3r,3ar,6s,6ar)-3,6-dihydroxy-3,3a,6,6a-tetrahydrofuro[3,2-b]furan-2,5-dione Chemical compound O1C(=O)[C@H](O)[C@H]2OC(=O)[C@@H](O)[C@H]21 QRFNDAVXJCGLFB-GJPGBQJBSA-N 0.000 description 3
- SXZYCXMUPBBULW-TXICZTDVSA-N D-glucono-1,4-lactone Chemical compound OC[C@@H](O)[C@H]1OC(=O)[C@H](O)[C@H]1O SXZYCXMUPBBULW-TXICZTDVSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000007273 lactonization reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- SXZYCXMUPBBULW-KLVWXMOXSA-N (3r,4s,5s)-5-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@H](O)[C@@H]1OC(=O)[C@H](O)[C@@H]1O SXZYCXMUPBBULW-KLVWXMOXSA-N 0.000 description 2
- SXZYCXMUPBBULW-SQOUGZDYSA-N (3s,4r,5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O SXZYCXMUPBBULW-SQOUGZDYSA-N 0.000 description 2
- CUOKHACJLGPRHD-HZLVTQRSSA-N (3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one Chemical compound OC[C@@H]1OC(=O)[C@@H](O)[C@H]1O CUOKHACJLGPRHD-HZLVTQRSSA-N 0.000 description 2
- SXZYCXMUPBBULW-MBMOQRBOSA-N (3s,4r,5s)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@@H](O)[C@@H]1OC(=O)[C@@H](O)[C@H]1O SXZYCXMUPBBULW-MBMOQRBOSA-N 0.000 description 2
- SXZYCXMUPBBULW-MGCNEYSASA-N (3s,4s,5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@@H](O)[C@H]1OC(=O)[C@@H](O)[C@@H]1O SXZYCXMUPBBULW-MGCNEYSASA-N 0.000 description 2
- SXZYCXMUPBBULW-FCAWWPLPSA-N (3s,4s,5s)-5-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@H](O)[C@@H]1OC(=O)[C@@H](O)[C@@H]1O SXZYCXMUPBBULW-FCAWWPLPSA-N 0.000 description 2
- SXZYCXMUPBBULW-GHWWWWGESA-N (5r)-5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-one Chemical compound OCC(O)[C@H]1OC(=O)C(O)C1O SXZYCXMUPBBULW-GHWWWWGESA-N 0.000 description 2
- SXZYCXMUPBBULW-UHFFFAOYSA-N 1,4-gluconolactone Natural products OCC(O)C1OC(=O)C(O)C1O SXZYCXMUPBBULW-UHFFFAOYSA-N 0.000 description 2
- BSPZKKBWTBYQOH-UHFFFAOYSA-N 3,4-dihydroxy-5-oxooxolane-2-carboxylic acid Chemical compound OC1C(O)C(=O)OC1C(O)=O BSPZKKBWTBYQOH-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- SXZYCXMUPBBULW-LECHCGJUSA-N D-(-)-Gulono-gamma-lactone Chemical compound OC[C@@H](O)[C@@H]1OC(=O)[C@H](O)[C@@H]1O SXZYCXMUPBBULW-LECHCGJUSA-N 0.000 description 2
- DSLZVSRJTYRBFB-YCAKELIYSA-N D-altraric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-YCAKELIYSA-N 0.000 description 2
- CUOKHACJLGPRHD-JJYYJPOSSA-N D-arabinono-1,4-lactone Chemical compound OC[C@H]1OC(=O)[C@@H](O)[C@@H]1O CUOKHACJLGPRHD-JJYYJPOSSA-N 0.000 description 2
- SXZYCXMUPBBULW-AIHAYLRMSA-N D-galactono-1,4-lactone Chemical compound OC[C@@H](O)[C@@H]1OC(=O)[C@H](O)[C@H]1O SXZYCXMUPBBULW-AIHAYLRMSA-N 0.000 description 2
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-KKQCNMDGSA-N D-gulonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-KKQCNMDGSA-N 0.000 description 2
- CUOKHACJLGPRHD-UZBSEBFBSA-N D-lyxono-1,4-lactone Chemical compound OC[C@H]1OC(=O)[C@@H](O)[C@H]1O CUOKHACJLGPRHD-UZBSEBFBSA-N 0.000 description 2
- CUOKHACJLGPRHD-BXXZVTAOSA-N D-ribono-1,4-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H]1O CUOKHACJLGPRHD-BXXZVTAOSA-N 0.000 description 2
- CUOKHACJLGPRHD-FLRLBIABSA-N D-xylono-1,4-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@H]1O CUOKHACJLGPRHD-FLRLBIABSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- DSLZVSRJTYRBFB-GJPGBQJBSA-N L-altraric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-GJPGBQJBSA-N 0.000 description 2
- QXKAIJAYHKCRRA-YVZJFKFKSA-N L-arabinonic acid Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)C(O)=O QXKAIJAYHKCRRA-YVZJFKFKSA-N 0.000 description 2
- CUOKHACJLGPRHD-YVZJFKFKSA-N L-arabinono-1,4-lactone Chemical compound OC[C@@H]1OC(=O)[C@H](O)[C@H]1O CUOKHACJLGPRHD-YVZJFKFKSA-N 0.000 description 2
- SXZYCXMUPBBULW-NEEWWZBLSA-N L-galactono-1,4-lactone Chemical compound OC[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@@H]1O SXZYCXMUPBBULW-NEEWWZBLSA-N 0.000 description 2
- DSLZVSRJTYRBFB-AJSXGEPRSA-N L-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-AJSXGEPRSA-N 0.000 description 2
- DSLZVSRJTYRBFB-ORZLYADOSA-N L-idaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-ORZLYADOSA-N 0.000 description 2
- QXKAIJAYHKCRRA-NUNKFHFFSA-N L-xylonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-NUNKFHFFSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 150000001299 aldehydes Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- ZQWFSIZRQANUDA-WQMSYZFBSA-L calcium;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxyhexanedioate;tetrahydrate Chemical compound O.O.O.O.[Ca+2].[O-]C(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O ZQWFSIZRQANUDA-WQMSYZFBSA-L 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000000457 gamma-lactone group Chemical group 0.000 description 2
- 235000012209 glucono delta-lactone Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- XECPAIJNBXCOBO-ZNIBRBMXSA-N (2R)-2-[(2R,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid Chemical compound O=C([C@H](O)[C@H]1[C@H](O)[C@@H](O)C(=O)O1)O XECPAIJNBXCOBO-ZNIBRBMXSA-N 0.000 description 1
- XECPAIJNBXCOBO-KXMYSMCESA-N (2R)-2-[(2S,3S,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid Chemical compound C1([C@H](O)[C@H](O)[C@@H]([C@@H](O)C(=O)O)O1)=O XECPAIJNBXCOBO-KXMYSMCESA-N 0.000 description 1
- BSPZKKBWTBYQOH-ADNNCPOWSA-N (2R,3R,4R)-3,4-dihydroxy-5-oxooxolane-2-carboxylic acid Chemical compound C1([C@H](O)[C@@H](O)[C@H](C(=O)O)O1)=O BSPZKKBWTBYQOH-ADNNCPOWSA-N 0.000 description 1
- XECPAIJNBXCOBO-CMPLKCRRSA-N (2S)-2-[(2R,3R,4S)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid Chemical compound O=C([C@@H](O)[C@H]1[C@H](O)[C@H](O)C(=O)O1)O XECPAIJNBXCOBO-CMPLKCRRSA-N 0.000 description 1
- RGHNJXZEOKUKBD-NRXMZTRTSA-N (2r,3r,4r,5s)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-NRXMZTRTSA-N 0.000 description 1
- KSJDOQFYNPUQDU-JJKGCWMISA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic acid;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O KSJDOQFYNPUQDU-JJKGCWMISA-N 0.000 description 1
- RGHNJXZEOKUKBD-NEEWWZBLSA-N (2r,3s,4s,5s)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-NEEWWZBLSA-N 0.000 description 1
- NPTTZSYLTYJCPR-MZJVJLTCSA-N (2r,4s)-2,3,4-trihydroxypentanedioic acid Chemical compound OC(=O)[C@@H](O)C(O)[C@@H](O)C(O)=O NPTTZSYLTYJCPR-MZJVJLTCSA-N 0.000 description 1
- BSPZKKBWTBYQOH-LAMMAJBHSA-N (2s,3r,4s)-3,4-dihydroxy-5-oxooxolane-2-carboxylic acid Chemical compound O[C@@H]1[C@H](O)C(=O)O[C@@H]1C(O)=O BSPZKKBWTBYQOH-LAMMAJBHSA-N 0.000 description 1
- RGHNJXZEOKUKBD-LECHCGJUSA-N (2s,3r,4s,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-LECHCGJUSA-N 0.000 description 1
- BSPZKKBWTBYQOH-ZPAAKOCQSA-N (2s,3s,4s)-3,4-dihydroxy-5-oxooxolane-2-carboxylic acid Chemical compound O[C@H]1[C@H](O)C(=O)O[C@@H]1C(O)=O BSPZKKBWTBYQOH-ZPAAKOCQSA-N 0.000 description 1
- RGHNJXZEOKUKBD-STGXQOJASA-N (2s,3s,4s,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-STGXQOJASA-N 0.000 description 1
- SXZYCXMUPBBULW-RSJOWCBRSA-N (3r,4r,5s)-5-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@H](O)[C@@H]1OC(=O)[C@H](O)[C@H]1O SXZYCXMUPBBULW-RSJOWCBRSA-N 0.000 description 1
- SXZYCXMUPBBULW-QMKXCQHVSA-N (3r,4s,5r)-5-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@H](O)[C@H]1OC(=O)[C@H](O)[C@@H]1O SXZYCXMUPBBULW-QMKXCQHVSA-N 0.000 description 1
- CUOKHACJLGPRHD-PZGQECOJSA-N (3r,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one Chemical compound OC[C@@H]1OC(=O)[C@H](O)[C@@H]1O CUOKHACJLGPRHD-PZGQECOJSA-N 0.000 description 1
- CQWFJIVHGWJYKB-UHNVWZDZSA-N (3s,4r)-3,4-dihydro-2h-pyran-3,4-diol Chemical compound O[C@H]1COC=C[C@H]1O CQWFJIVHGWJYKB-UHNVWZDZSA-N 0.000 description 1
- SXZYCXMUPBBULW-VRUJNKQUSA-N (3s,4s,5r)-5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-one Chemical compound OCC(O)[C@H]1OC(=O)[C@@H](O)[C@@H]1O SXZYCXMUPBBULW-VRUJNKQUSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NPTTZSYLTYJCPR-UHFFFAOYSA-N 2,3,4-trihydroxypentanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)C(O)=O NPTTZSYLTYJCPR-UHFFFAOYSA-N 0.000 description 1
- BUBVLQDEIIUIQG-UHFFFAOYSA-N 3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one Chemical compound C=1C=CC=CC=1COC1C(OCC=2C=CC=CC=2)C(OCC=2C=CC=CC=2)C(=O)OC1COCC1=CC=CC=C1 BUBVLQDEIIUIQG-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- QXKAIJAYHKCRRA-BXXZVTAOSA-N D-ribonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O QXKAIJAYHKCRRA-BXXZVTAOSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RGHNJXZEOKUKBD-RSJOWCBRSA-N L-galactonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-RSJOWCBRSA-N 0.000 description 1
- RGHNJXZEOKUKBD-KLVWXMOXSA-N L-gluconic acid Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-KLVWXMOXSA-N 0.000 description 1
- SXZYCXMUPBBULW-SKNVOMKLSA-N L-gulono-1,4-lactone Chemical compound OC[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O SXZYCXMUPBBULW-SKNVOMKLSA-N 0.000 description 1
- QXKAIJAYHKCRRA-PZGQECOJSA-N L-lyxonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)C(O)=O QXKAIJAYHKCRRA-PZGQECOJSA-N 0.000 description 1
- CUOKHACJLGPRHD-NUNKFHFFSA-N L-xylono-1,4-lactone Chemical compound OC[C@@H]1OC(=O)[C@@H](O)[C@@H]1O CUOKHACJLGPRHD-NUNKFHFFSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- DSLZVSRJTYRBFB-GNSDDBTRSA-N allaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-GNSDDBTRSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 159000000006 cesium salts Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000422 delta-lactone group Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- CUOKHACJLGPRHD-UHFFFAOYSA-N gamma-Lacton der l-Arabonsaeure Natural products OCC1OC(=O)C(O)C1O CUOKHACJLGPRHD-UHFFFAOYSA-N 0.000 description 1
- 229960003681 gluconolactone Drugs 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58483504P | 2004-06-30 | 2004-06-30 | |
| US58483204P | 2004-06-30 | 2004-06-30 | |
| PCT/US2005/023815 WO2006005070A1 (en) | 2004-06-30 | 2005-06-30 | Synthesis of aldonolactones, aldarolactones, and aldarodilactones using gas sparging |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008505122A true JP2008505122A (ja) | 2008-02-21 |
| JP2008505122A5 JP2008505122A5 (enExample) | 2008-06-26 |
Family
ID=35058776
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007519536A Pending JP2008505122A (ja) | 2004-06-30 | 2005-06-30 | ガススパージングを用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 |
| JP2007519537A Pending JP2008515769A (ja) | 2004-06-30 | 2005-06-30 | 共沸蒸留を用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007519537A Pending JP2008515769A (ja) | 2004-06-30 | 2005-06-30 | 共沸蒸留を用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 |
Country Status (4)
| Country | Link |
|---|---|
| EP (2) | EP1773838A1 (enExample) |
| JP (2) | JP2008505122A (enExample) |
| CA (2) | CA2571774A1 (enExample) |
| WO (2) | WO2006005071A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008505122A (ja) * | 2004-06-30 | 2008-02-21 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ガススパージングを用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 |
| US8501989B2 (en) | 2009-06-13 | 2013-08-06 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US8669397B2 (en) | 2009-06-13 | 2014-03-11 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| EP2440513B1 (en) | 2009-06-13 | 2018-08-22 | Archer-Daniels-Midland Company | Production of glutaric acid and derivatives from carbohydrate-containing materials |
| US8669393B2 (en) | 2010-03-05 | 2014-03-11 | Rennovia, Inc. | Adipic acid compositions |
| US9770705B2 (en) | 2010-06-11 | 2017-09-26 | Rennovia Inc. | Oxidation catalysts |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5312967A (en) * | 1992-08-12 | 1994-05-17 | Uab Research Foundation | Process for making activated aldarate esters, ester/lactones and lactones |
| US6049004A (en) * | 1998-12-11 | 2000-04-11 | Kiely; Donald E. | Nitric acid removal from oxidation products |
| US20020028959A1 (en) * | 2000-05-26 | 2002-03-07 | Andrews Mark Allen | Process for the manufacture of anhydro sugar alcohols with the assistance of a gas purge |
| JP2003096071A (ja) * | 2001-08-27 | 2003-04-03 | Cheil Jedang Corp | スタチンの製造におけるラクトン化方法 |
| JP2008515769A (ja) * | 2004-06-30 | 2008-05-15 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 共沸蒸留を用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1830618A (en) * | 1930-04-12 | 1931-11-03 | Pfizer Charles & Co | Production of lactones |
| GB613444A (en) * | 1946-01-17 | 1948-11-29 | John George Mackay Bremner | Improvements in and relating to the production of heterocyclic compounds |
| US4581465A (en) * | 1984-03-16 | 1986-04-08 | The Dow Chemical Company | Preparation of 1,4-lactones of 3,6-anhydrohexanoic acids |
| FI92051C (fi) * | 1992-03-17 | 1994-09-26 | Amylum Nv | Menetelmä ksylitolin valmistamiseksi D-glukoosista ja D-glukoosin ja D-fruktoosin sekä D-glukoosin ja D-galaktoosin seoksista |
| US20060093702A1 (en) * | 2004-07-28 | 2006-05-04 | Andersen Keith C | Encapsulation mold assembly and interchangeable cartridge |
-
2005
- 2005-06-30 JP JP2007519536A patent/JP2008505122A/ja active Pending
- 2005-06-30 CA CA002571774A patent/CA2571774A1/en not_active Abandoned
- 2005-06-30 WO PCT/US2005/023816 patent/WO2006005071A1/en not_active Ceased
- 2005-06-30 CA CA002571060A patent/CA2571060A1/en not_active Abandoned
- 2005-06-30 EP EP05769130A patent/EP1773838A1/en not_active Withdrawn
- 2005-06-30 JP JP2007519537A patent/JP2008515769A/ja active Pending
- 2005-06-30 WO PCT/US2005/023815 patent/WO2006005070A1/en not_active Ceased
- 2005-06-30 EP EP05787937A patent/EP1773839A1/en not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5312967A (en) * | 1992-08-12 | 1994-05-17 | Uab Research Foundation | Process for making activated aldarate esters, ester/lactones and lactones |
| US6049004A (en) * | 1998-12-11 | 2000-04-11 | Kiely; Donald E. | Nitric acid removal from oxidation products |
| US20020028959A1 (en) * | 2000-05-26 | 2002-03-07 | Andrews Mark Allen | Process for the manufacture of anhydro sugar alcohols with the assistance of a gas purge |
| JP2003096071A (ja) * | 2001-08-27 | 2003-04-03 | Cheil Jedang Corp | スタチンの製造におけるラクトン化方法 |
| JP2008515769A (ja) * | 2004-06-30 | 2008-05-15 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 共沸蒸留を用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006005071A1 (en) | 2006-01-12 |
| EP1773839A1 (en) | 2007-04-18 |
| CA2571060A1 (en) | 2006-01-12 |
| EP1773838A1 (en) | 2007-04-18 |
| CA2571774A1 (en) | 2006-01-12 |
| WO2006005070A1 (en) | 2006-01-12 |
| JP2008515769A (ja) | 2008-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Shiina et al. | A new condensation reaction for the synthesis of carboxylic esters from nearly equimolar amounts of carboxylic acids and alcohols using 2-methyl-6-nitrobenzoic anhydride | |
| EP0915866B1 (en) | Improved process for the synthesis of protected esters of (s)-3,4-dihydroxybutyric acid | |
| JP2005506984A5 (enExample) | ||
| JP5395908B2 (ja) | ４−（１−ヒドロキシ−１−メチルエチル）−２−プロピルイミダゾール−５−カルボン酸エステルの製造方法 | |
| US20060084800A1 (en) | Synthesis of aldonolactones, aldarolactones, and aldarodilactones using azeotropic distillation | |
| JP2008505122A (ja) | ガススパージングを用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 | |
| US20060084817A1 (en) | Synthesis of aldonolactones, aldarolactones, and aldarodilactones using gas sparging | |
| HU196162B (en) | Process for producing erythrodiols | |
| JPWO2005040246A1 (ja) | アシロキシ酢酸重合体およびその製造方法 | |
| CN101553477A (zh) | 制备醛糖酸及其衍生物的方法 | |
| EP1167365B1 (en) | Method of producing sesamol formic acid ester and sesamol | |
| JP2006036710A (ja) | 光学活性な３−ヒドロキシテトラヒドロフランの製造法 | |
| JP4653966B2 (ja) | ２−ベンゾイルオキシアセトアルデヒド誘導体の製造法 | |
| JP2001302653A (ja) | ラクトンの製造方法 | |
| RU2455296C2 (ru) | Способ получения альдоновых кислот и их производных | |
| CN117105891B (zh) | 一种dbdmh促进的苯并呋喃类化合物的合成方法 | |
| JP3047582B2 (ja) | トレオ−４−アルコキシ−５−（アリールヒドロキシメチル）−２（５ｈ）−フラノンの製造方法 | |
| Tkachenko et al. | A new route of the oxidative cleavage of substituted carbonylfurans as an approach to 4-oxobutanoic acids | |
| JPH03101672A (ja) | ２，５―フランジカルボキシアルデヒドの製法 | |
| JPS584695B2 (ja) | シクロペンテノン誘導体の製造法 | |
| JP4365602B2 (ja) | 光学活性トランス−３−シクロヘキシル−オキシランカルボン酸の製造方法 | |
| Horneman et al. | Highly Functionalised Cyclopentanes by Radical Cyclisation of Unsaturated Bromolactones III. Preparation of Carbaaldohexofuranoses. Determination of the Relative Configuration at C-4/C-5 of 2, 3-Unsaturated Heptono-1, 4-lactones by Means of 1H NMR Spectroscopy | |
| HU214626B (hu) | Eljárás R-glicerin-aldehid-3-pentanid előállítására | |
| JP3610483B2 (ja) | ５−ホルミル−３−ヒドロキシメチルシクロヘキサン−１−カルボン酸化合物及びそれらの製造方法 | |
| KR100469944B1 (ko) | 히드록시테트라히드로퓨란의제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20080303 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080502 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080502 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20080912 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20080912 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20081025 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110802 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20120110 |