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【结 构 式】

【分子编号】45587

【品名】2-(trimethylsilyl)ethyl (3S,4S,6S)-4-hydroxy-6-[[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-3-methoxytetrahydro-2H-pyran-2-yl]methoxy]tetrahydro-2H-pyran-3-yl(methyl)carbamate

【CA登记号】

【 分 子 式 】C19H37NO10Si

【 分 子 量 】467.58902

【元素组成】C 48.81% H 7.98% N 3% O 34.22% Si 6.01%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VII)

The Grignard condensation of pyrrolinedione (I) with 7-chloroindol-1-ylmagnesium bromide (II) in toluene gives the monoaddition product (III), which is condensed with indol-1-ylmagnesium bromide (IV) to yield the disubstituted compound (V). The hydrogenation of (V) with H2 over Pd/C in DMF affords the tetrahydro derivative (VI), which is condensed with the aminosugar (VII) in DMF and dehydrogenated with DDQ or DBU to afford the adduct (VIII). Finally, the methylamino group of (VIII) is deprotected by means of TBAF in THF.

1 Van Vranken, D.L.; Chisholm, J.D.; Regiocontrolled synthesis of the antitumor antibiotic AT2433-A1. J Org Chem 2000, 65, 22, 7541.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 31468 3,4-dibromo-1-methyl-1H-pyrrole-2,5-dione C5H3Br2NO2 详情 详情
(II) 45582 bromo(7-chloro-1H-indol-1-yl)magnesium C8H5BrClMgN 详情 详情
(III) 45583 3-bromo-4-(7-chloro-1H-inden-3-yl)-1-methyl-1H-pyrrole-2,5-dione C14H9BrClNO2 详情 详情
(IV) 45584 bromo(1H-indol-1-yl)magnesium C8H6BrMgN 详情 详情
(V) 45585 3-(7-chloro-1H-indol-3-yl)-4-(1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione C21H14ClN3O2 详情 详情
(VI) 45586 (4bR,4cR,7aR,12bS)-1-chloro-6-methyl-7a,12,12b,13-tetrahydro-4bH-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(4cH,6H)-dione 577-59-3 C21H16ClN3O2 详情 详情
(VII) 45587 2-(trimethylsilyl)ethyl (3S,4S,6S)-4-hydroxy-6-[[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-3-methoxytetrahydro-2H-pyran-2-yl]methoxy]tetrahydro-2H-pyran-3-yl(methyl)carbamate C19H37NO10Si 详情 详情
(VIII) 45588 2-(trimethylsilyl)ethyl (3S,4S,6S)-6-[[(2R,3S,4R,5R,6R)-6-(11-chloro-6-methyl-5,7-dioxo-5,6,7,13-tetrahydro-12H-indolo[2,3-a]pyrrolo[3,4-c]carbazol-12-yl)-4,5-dihydroxy-3-methoxytetrahydro-2H-pyran-2-yl]methoxy]-4-hydroxytetrahydro-2H-pyran-3-yl(methyl)carbamate C40H47ClN4O11Si 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VII)

The intermediate aminosugar (VII) has been obtained as follows: The protection of the alcohol (IX) with Bn-Br and NaH in DMF gives the benzyl ether (X), which is oxidized with OsO4 and NaIO4 in acetone/THF to yield the aldehyde (XI). The cyclization of (XI) by means of Ts-OH in dioxane/water affords the lactol (XII), which is treated with diethylamino sulfurtrifluoride (DAST) to provide the glycosyl fluoride (XIII). The condensation of (XIII) with the benzylated glucose derivative (XIV) by means of AgClO4 and SnCl2 in THF/ethyl ether gives the disaccharide (XV). The reduction of the carbamoyl group of (XV) with LiAlH4 in refluxing THF yields the methylamino derivative (XVI), which is protected at the methylamino group with trimethylsilylethyl(p-methylphenyl)carbonate (teoc-O-PNP) to afford the carbamate (XVII). Finally, this compound is debenzylated by hydrogenation over Pd/C in ethanol/THF to afford the target aminosugar (VIII).

1 Van Vranken, D.L.; Chisholm, J.D.; Regiocontrolled synthesis of the antitumor antibiotic AT2433-A1. J Org Chem 2000, 65, 22, 7541.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 45587 2-(trimethylsilyl)ethyl (3S,4S,6S)-4-hydroxy-6-[[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-3-methoxytetrahydro-2H-pyran-2-yl]methoxy]tetrahydro-2H-pyran-3-yl(methyl)carbamate C19H37NO10Si 详情 详情
(IX) 45589 tert-butyl (4S)-4-(1-hydroxy-3-butenyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate C14H25NO4 详情 详情
(X) 45590 tert-butyl (4S)-4-[1-(benzyloxy)-3-butenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 15930-53-7 C21H31NO4 详情 详情
(XI) 45591 tert-butyl (4S)-4-[1-(benzyloxy)-3-oxopropyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate C20H29NO5 详情 详情
(XII) 45592 tert-butyl (3S,4S)-4-(benzyloxy)-6-hydroxytetrahydro-2H-pyran-3-ylcarbamate C17H25NO5 详情 详情
(XIII) 45593 tert-butyl (3S,4S)-4-(benzyloxy)-6-fluorotetrahydro-2H-pyran-3-ylcarbamate C17H24FNO4 详情 详情
(XIV) 45594 [(2R,3S,4S,5R,6R)-4,5,6-tris(benzyloxy)-3-methoxytetrahydro-2H-pyran-2-yl]methanol C28H32O6 详情 详情
(XV) 45595 tert-butyl (3S,4S,6S)-4-(benzyloxy)-6-[[(2R,3S,4S,5R,6R)-4,5,6-tris(benzyloxy)-3-methoxytetrahydro-2H-pyran-2-yl]methoxy]tetrahydro-2H-pyran-3-ylcarbamate C45H55NO10 详情 详情
(XVI) 45596 N-((3S,4S,6S)-4-(benzyloxy)-6-[[(2R,3S,4S,5R,6R)-4,5,6-tris(benzyloxy)-3-methoxytetrahydro-2H-pyran-2-yl]methoxy]tetrahydro-2H-pyran-3-yl)-N-methylamine; (3S,4S,6S)-4-(benzyloxy)-N-methyl-6-[[(2R,3S,4S,5R,6R)-4,5,6-tris(benzyloxy)-3-methoxytetrahydro-2H-pyran-2-yl]methoxy]tetrahydro-2H-pyran-3-amine C41H49NO8 详情 详情
(XVII) 45597 2-(trimethylsilyl)ethyl (3S,4S,6S)-4-(benzyloxy)-6-[[(2R,3S,4S,5R,6R)-4,5,6-tris(benzyloxy)-3-methoxytetrahydro-2H-pyran-2-yl]methoxy]tetrahydro-2H-pyran-3-yl(methyl)carbamate C47H61NO10Si 详情 详情
Extended Information