BR112020000141A2 - síntese de halicondrinas - Google Patents

Info

Publication number

BR112020000141A2

BR112020000141A2 BR112020000141-4A BR112020000141A BR112020000141A2 BR 112020000141 A2 BR112020000141 A2 BR 112020000141A2 BR 112020000141 A BR112020000141 A BR 112020000141A BR 112020000141 A2 BR112020000141 A2 BR 112020000141A2

Authority

BR

Brazil

Prior art keywords

optionally substituted

fact

compound

formula

salt

Prior art date

2017-07-06

Links

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• Global Dossier
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• 238000003786 synthesis reaction Methods 0.000 title abstract description 33
• 230000015572 biosynthetic process Effects 0.000 title abstract description 32
• 238000000034 method Methods 0.000 claims abstract description 501
• 150000001875 compounds Chemical class 0.000 claims abstract description 436
• 238000006243 chemical reaction Methods 0.000 claims abstract description 75
• 238000005859 coupling reaction Methods 0.000 claims abstract description 70
• 229910052739 hydrogen Inorganic materials 0.000 claims description 503
• 239000001257 hydrogen Substances 0.000 claims description 503
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 446
• 150000003839 salts Chemical class 0.000 claims description 372
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 292
• 125000002252 acyl group Chemical group 0.000 claims description 278
• 125000000623 heterocyclic group Chemical group 0.000 claims description 268
• 229910052736 halogen Inorganic materials 0.000 claims description 210
• 150000002367 halogens Chemical group 0.000 claims description 210
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 183
• -1 azide salt Chemical class 0.000 claims description 154
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 147
• 125000001072 heteroaryl group Chemical group 0.000 claims description 136
• 125000004429 atom Chemical group 0.000 claims description 135
• 125000000217 alkyl group Chemical group 0.000 claims description 97
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 91
• 125000003107 substituted aryl group Chemical group 0.000 claims description 91
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 85
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 81
• 229910052759 nickel Inorganic materials 0.000 claims description 73
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 62
• 230000008878 coupling Effects 0.000 claims description 60
• 238000010168 coupling process Methods 0.000 claims description 60
• 229910052760 oxygen Inorganic materials 0.000 claims description 59
• 239000003153 chemical reaction reagent Substances 0.000 claims description 55
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
• QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 35
• 229910052726 zirconium Inorganic materials 0.000 claims description 35
• 238000007363 ring formation reaction Methods 0.000 claims description 34
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Substances CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 31
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 31
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 29
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical group [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 26
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 25
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 25
• 239000003446 ligand Substances 0.000 claims description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical group CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 22
• DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 claims description 22
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 21
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 19
• 229910001868 water Inorganic materials 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
• 230000003647 oxidation Effects 0.000 claims description 15
• 238000007254 oxidation reaction Methods 0.000 claims description 15
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
• 125000005647 linker group Chemical group 0.000 claims description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
• 229940124530 sulfonamide Drugs 0.000 claims description 11
• 239000011701 zinc Substances 0.000 claims description 11
• XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 10
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
• LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 239000000203 mixture Substances 0.000 claims description 10
• 239000002904 solvent Substances 0.000 claims description 10
• 229910052725 zinc Inorganic materials 0.000 claims description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
• 150000001412 amines Chemical class 0.000 claims description 9
• AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical group [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 9
• ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 claims description 9
• 150000003456 sulfonamides Chemical class 0.000 claims description 9
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 239000011230 binding agent Substances 0.000 claims description 8
• 239000011651 chromium Substances 0.000 claims description 8
• 235000019439 ethyl acetate Nutrition 0.000 claims description 8
• 239000011572 manganese Substances 0.000 claims description 8
• 229910052751 metal Inorganic materials 0.000 claims description 8
• TXNLQUKVUJITMX-UHFFFAOYSA-N 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine Chemical group CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 TXNLQUKVUJITMX-UHFFFAOYSA-N 0.000 claims description 7
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 7
• 150000001540 azides Chemical class 0.000 claims description 7
• 230000003197 catalytic effect Effects 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 7
• 239000002184 metal Substances 0.000 claims description 7
• STMPXDBGVJZCEX-UHFFFAOYSA-N triethylsilyl trifluoromethanesulfonate Chemical compound CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F STMPXDBGVJZCEX-UHFFFAOYSA-N 0.000 claims description 7
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 239000011630 iodine Substances 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
• CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims description 5
• XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 5
• YEKPNMQQSPHKBP-UHFFFAOYSA-N 2-methyl-6-nitrobenzoic anhydride Chemical group CC1=CC=CC([N+]([O-])=O)=C1C(=O)OC(=O)C1=C(C)C=CC=C1[N+]([O-])=O YEKPNMQQSPHKBP-UHFFFAOYSA-N 0.000 claims description 5
• AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 claims description 5
• FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 claims description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
• 125000002837 carbocyclic group Chemical group 0.000 claims description 5
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical group C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 5
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 5
• CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 5
• 229910019142 PO4 Inorganic materials 0.000 claims description 4
• 125000004450 alkenylene group Chemical group 0.000 claims description 4
• 125000000732 arylene group Chemical group 0.000 claims description 4
• 230000001351 cycling effect Effects 0.000 claims description 4
• 125000004474 heteroalkylene group Chemical group 0.000 claims description 4
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical group [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 4
• 239000012038 nucleophile Substances 0.000 claims description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
• 239000010452 phosphate Substances 0.000 claims description 4
• IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical group C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims description 4
• 239000010936 titanium Substances 0.000 claims description 4
• FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims description 4
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
• 229910021585 Nickel(II) bromide Inorganic materials 0.000 claims description 3
• 239000008186 active pharmaceutical agent Substances 0.000 claims description 3
• 230000000536 complexating effect Effects 0.000 claims description 3
• 229910052802 copper Inorganic materials 0.000 claims description 3
• 239000010949 copper Substances 0.000 claims description 3
• 238000002156 mixing Methods 0.000 claims description 3
• IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical group [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 claims description 3
• 239000012285 osmium tetroxide Substances 0.000 claims description 3
• 229910000489 osmium tetroxide Inorganic materials 0.000 claims description 3
• 239000011591 potassium Substances 0.000 claims description 3
• 229910052700 potassium Inorganic materials 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 2
• YSAVZVORKRDODB-OLQVQODUSA-N diethyl (2r,3s)-2,3-dihydroxybutanedioate Chemical compound CCOC(=O)[C@@H](O)[C@@H](O)C(=O)OCC YSAVZVORKRDODB-OLQVQODUSA-N 0.000 claims description 2
• 125000005549 heteroarylene group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 417
• 241001516584 Andrya Species 0.000 claims 31
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 16
• 150000001336 alkenes Chemical class 0.000 claims 15
• 238000010511 deprotection reaction Methods 0.000 claims 15
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 15
• PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 14
• 150000004678 hydrides Chemical class 0.000 claims 13
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 13
• LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 12
• 230000001590 oxidative effect Effects 0.000 claims 9
• 238000006177 thiolation reaction Methods 0.000 claims 9
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims 8
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims 8
• 125000001979 organolithium group Chemical group 0.000 claims 7
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 6
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical group [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 6
• 229910003002 lithium salt Inorganic materials 0.000 claims 6
• 159000000002 lithium salts Chemical class 0.000 claims 6
• 238000006735 epoxidation reaction Methods 0.000 claims 5
• 229910052748 manganese Inorganic materials 0.000 claims 5
• 238000006884 silylation reaction Methods 0.000 claims 5
• BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical group CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 claims 4
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 4
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 4
• 239000002841 Lewis acid Substances 0.000 claims 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
• 150000007517 lewis acids Chemical class 0.000 claims 4
• 150000002978 peroxides Chemical class 0.000 claims 4
• 239000002516 radical scavenger Substances 0.000 claims 4
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical group CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 4
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical group [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 4
• HVHZEKKZMFRULH-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylpyridine Chemical group CC1=CC(C(C)(C)C)=NC(C(C)(C)C)=C1 HVHZEKKZMFRULH-UHFFFAOYSA-N 0.000 claims 3
• 101150015512 OSBPL10 gene Proteins 0.000 claims 3
• 102100031469 Oxysterol-binding protein-related protein 10 Human genes 0.000 claims 3
• 241000610375 Sparisoma viride Species 0.000 claims 3
• 238000004440 column chromatography Methods 0.000 claims 3
• 238000006197 hydroboration reaction Methods 0.000 claims 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical group [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
• GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims 3
• AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 2
• 101100020619 Arabidopsis thaliana LATE gene Proteins 0.000 claims 2
• VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 2
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
• 102100026060 Exosome component 10 Human genes 0.000 claims 2
• 101001055976 Homo sapiens Exosome component 10 Proteins 0.000 claims 2
• 101000992388 Homo sapiens Oxysterol-binding protein-related protein 8 Proteins 0.000 claims 2
• 239000012448 Lithium borohydride Substances 0.000 claims 2
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 2
• 102100032151 Oxysterol-binding protein-related protein 8 Human genes 0.000 claims 2
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical group [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 2
• 150000001409 amidines Chemical class 0.000 claims 2
• 150000008064 anhydrides Chemical class 0.000 claims 2
• QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical class OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 claims 2
• 229910052804 chromium Inorganic materials 0.000 claims 2
• 239000002361 compost Substances 0.000 claims 2
• JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims 2
• 238000005906 dihydroxylation reaction Methods 0.000 claims 2
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 2
• 230000036571 hydration Effects 0.000 claims 2
• 238000006703 hydration reaction Methods 0.000 claims 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 2
• JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 2
• ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical group [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 claims 2
• 229910052754 neon Inorganic materials 0.000 claims 2
• GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 claims 2
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 2
• 239000000843 powder Substances 0.000 claims 2
• 238000001953 recrystallisation Methods 0.000 claims 2
• 239000000741 silica gel Substances 0.000 claims 2
• 229910002027 silica gel Inorganic materials 0.000 claims 2
• 238000006277 sulfonation reaction Methods 0.000 claims 2
• 229910052719 titanium Inorganic materials 0.000 claims 2
• VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical group CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims 2
• 125000005270 trialkylamine group Chemical group 0.000 claims 2
• JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 claims 2
• 229910052720 vanadium Inorganic materials 0.000 claims 2
• LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 2
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