NO312033B1 - Fremgangsmåte for selektiv oksydasjon av prim¶re alkoholer av oligosakarider - Google Patents
Fremgangsmåte for selektiv oksydasjon av prim¶re alkoholer av oligosakarider Download PDFInfo
- Publication number
- NO312033B1 NO312033B1 NO19993892A NO993892A NO312033B1 NO 312033 B1 NO312033 B1 NO 312033B1 NO 19993892 A NO19993892 A NO 19993892A NO 993892 A NO993892 A NO 993892A NO 312033 B1 NO312033 B1 NO 312033B1
- Authority
- NO
- Norway
- Prior art keywords
- oligosaccharides
- selective oxidation
- alcohols
- reaction
- dimethylhydantoin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 35
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 25
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 24
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 23
- 230000003647 oxidation Effects 0.000 title claims abstract description 22
- 150000003138 primary alcohols Chemical class 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000007800 oxidant agent Substances 0.000 claims abstract description 10
- 230000003197 catalytic effect Effects 0.000 claims abstract description 7
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001298 alcohols Chemical class 0.000 claims abstract description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 3
- 230000007935 neutral effect Effects 0.000 claims abstract description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 229920002683 Glycosaminoglycan Polymers 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 abstract description 4
- 150000007942 carboxylates Chemical group 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- -1 alkyl nitroxyl Chemical group 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000002785 anti-thrombosis Effects 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002772 monosaccharides Chemical class 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 description 1
- 229920001287 Chondroitin sulfate Polymers 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229920000045 Dermatan sulfate Polymers 0.000 description 1
- 229920002971 Heparan sulfate Polymers 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- AVJBPWGFOQAPRH-FWMKGIEWSA-N alpha-L-IdopA-(1->3)-beta-D-GalpNAc4S Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS(O)(=O)=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](C(O)=O)O1 AVJBPWGFOQAPRH-FWMKGIEWSA-N 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 150000001720 carbohydrates Chemical group 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 229940059329 chondroitin sulfate Drugs 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical group 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229940051593 dermatan sulfate Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/033—Uronic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98202709 | 1998-08-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO993892D0 NO993892D0 (no) | 1999-08-12 |
| NO993892L NO993892L (no) | 2000-02-14 |
| NO312033B1 true NO312033B1 (no) | 2002-03-04 |
Family
ID=8234032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19993892A NO312033B1 (no) | 1998-08-13 | 1999-08-12 | Fremgangsmåte for selektiv oksydasjon av prim¶re alkoholer av oligosakarider |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6310200B1 (ko) |
| EP (1) | EP0979826B1 (ko) |
| JP (1) | JP4852689B2 (ko) |
| KR (1) | KR100566354B1 (ko) |
| AT (1) | ATE227303T1 (ko) |
| AU (1) | AU750955B2 (ko) |
| BR (1) | BR9903619B1 (ko) |
| CA (1) | CA2278402C (ko) |
| DE (1) | DE69903774T2 (ko) |
| DK (1) | DK0979826T3 (ko) |
| ES (1) | ES2187116T3 (ko) |
| NO (1) | NO312033B1 (ko) |
| PT (1) | PT979826E (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6540876B1 (en) | 2000-05-19 | 2003-04-01 | National Starch And Chemical Ivnestment Holding Corporation | Use of amide or imide co-catalysts for nitroxide mediated oxidation |
| AU2002219718A1 (en) * | 2000-12-13 | 2002-06-24 | Sca Hygiene Products Zeist B.V. | Process for oxidising primary alcohols |
| CN1886427B (zh) | 2003-11-28 | 2012-05-23 | 伊士曼化工公司 | 纤维素共聚体和氧化方法 |
| WO2013011459A1 (en) | 2011-07-18 | 2013-01-24 | Ranbaxy Laboratories Limited | Process for the preparation of fondaparinux |
| WO2013011442A1 (en) | 2011-07-18 | 2013-01-24 | Ranbaxy Laboratories Limited | Process for preparation of fondaparinux and its intermediates |
| CN102826979B (zh) * | 2012-07-04 | 2014-12-24 | 华东师范大学 | 用二溴海因将苄醇选择性氧化为苯甲醛和苯甲酸甲酯类化合物的方法 |
| CN102898487B (zh) * | 2012-11-13 | 2016-03-09 | 麦科罗夫（南通）生物制药有限公司 | 一种磺达肝葵钠二糖中间体片段ba及其合成方法 |
| CN106167496B (zh) * | 2016-07-20 | 2018-07-10 | 陕西师范大学 | 一种桥环内酯类化合物及其制备方法和在构建β-甘露糖苷键中的应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX173174B (es) | 1989-11-06 | 1994-02-04 | Bio Lab Inc | Composiciones de n-halogeno con pigmento azul estable |
| NL194919C (nl) | 1993-09-07 | 2003-07-04 | Tno | Werkwijze voor het oxideren van koolhydraten. |
| US5821374A (en) * | 1995-11-21 | 1998-10-13 | Hoffmann-La Roche Inc. | Process for the oxidation of alcohols |
| FR2742755B1 (fr) | 1995-12-21 | 1998-02-20 | Roquette Freres | Procede perfectionne d'oxydation des sucres |
-
1999
- 1999-07-20 US US09/357,502 patent/US6310200B1/en not_active Expired - Lifetime
- 1999-07-22 CA CA002278402A patent/CA2278402C/en not_active Expired - Lifetime
- 1999-08-03 JP JP21977499A patent/JP4852689B2/ja not_active Expired - Lifetime
- 1999-08-09 ES ES99202600T patent/ES2187116T3/es not_active Expired - Lifetime
- 1999-08-09 DE DE69903774T patent/DE69903774T2/de not_active Expired - Lifetime
- 1999-08-09 PT PT99202600T patent/PT979826E/pt unknown
- 1999-08-09 DK DK99202600T patent/DK0979826T3/da active
- 1999-08-09 AT AT99202600T patent/ATE227303T1/de active
- 1999-08-09 EP EP99202600A patent/EP0979826B1/en not_active Expired - Lifetime
- 1999-08-12 NO NO19993892A patent/NO312033B1/no not_active IP Right Cessation
- 1999-08-12 AU AU44443/99A patent/AU750955B2/en not_active Expired
- 1999-08-12 KR KR1019990033036A patent/KR100566354B1/ko not_active IP Right Cessation
- 1999-08-12 BR BRPI9903619-3A patent/BR9903619B1/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO993892D0 (no) | 1999-08-12 |
| DE69903774T2 (de) | 2003-07-03 |
| EP0979826B1 (en) | 2002-11-06 |
| NO993892L (no) | 2000-02-14 |
| JP2000109494A (ja) | 2000-04-18 |
| PT979826E (pt) | 2003-01-31 |
| AU750955B2 (en) | 2002-08-01 |
| US6310200B1 (en) | 2001-10-30 |
| EP0979826A1 (en) | 2000-02-16 |
| BR9903619B1 (pt) | 2011-09-06 |
| CA2278402C (en) | 2008-09-02 |
| CA2278402A1 (en) | 2000-02-13 |
| KR20000017265A (ko) | 2000-03-25 |
| ATE227303T1 (de) | 2002-11-15 |
| ES2187116T3 (es) | 2003-05-16 |
| BR9903619A (pt) | 2000-09-19 |
| AU4444399A (en) | 2000-03-09 |
| KR100566354B1 (ko) | 2006-03-31 |
| DE69903774D1 (de) | 2002-12-12 |
| DK0979826T3 (da) | 2003-03-03 |
| JP4852689B2 (ja) | 2012-01-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |