tert-butyl (4S)-4-[1-(benzyloxy)-3-oxopropyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】45591

【品名】tert-butyl (4S)-4-[1-(benzyloxy)-3-oxopropyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

【CA登记号】

【分子式】C₂₀H₂₉NO₅

【分子量】363.454

【元素组成】C 66.09% H 8.04% N 3.85% O 22.01%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XI)

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).

参考文献中间体

合成目标

【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

合成路线2

该中间体在本合成路线中的序号：(VI)

The intermediate aminosugar (III) has been obtained as follows: The protection of the alcohol (IV) with Bn-Br and NaH in DMF gives the benzyl ether (V), which is oxidized with OsO4 and NaIO4 in acetone/THF to yield the aldehyde (VI). The cyclization of (VI) by means of TsOH in dioxane/water affords the lactol (VII), which is treated with diethylamino sulfurtrifluoride (DAST) to provide the glycosyl fluoride (VIII). The condensation of (VIII) with the benzylated glucose derivative (IX) by means of AgClO4 and SnCl2 in THF/ethyl ether gives the disaccharide (X). The reduction of the carbamoyl group of (X) with LiAlH4 in refluxing THF yields the methylamino derivative (XI), which is finally debenzylated by hydrogenation over Pd/C in ethanol/THF to afford the target aminosugar (III).

参考文献中间体

合成目标

【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
(III)	45599	(3R,4R,5S,6R)-6-([[(2S,4S,5S)-4-hydroxy-5-(methylamino)tetrahydro-2H-pyran-2-yl]oxy]methyl)-5-methoxytetrahydro-2H-pyran-2,3,4-triol		C₁₃H₂₅NO₈	详情	详情
(IV)	45589	tert-butyl (4S)-4-(1-hydroxy-3-butenyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate		C₁₄H₂₅NO₄	详情	详情
(V)	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
(VI)	45591	tert-butyl (4S)-4-[1-(benzyloxy)-3-oxopropyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate		C₂₀H₂₉NO₅	详情	详情
(VII)	45592	tert-butyl (3S,4S)-4-(benzyloxy)-6-hydroxytetrahydro-2H-pyran-3-ylcarbamate		C₁₇H₂₅NO₅	详情	详情
(VIII)	45593	tert-butyl (3S,4S)-4-(benzyloxy)-6-fluorotetrahydro-2H-pyran-3-ylcarbamate		C₁₇H₂₄FNO₄	详情	详情
(IX)	45594	[(2R,3S,4S,5R,6R)-4,5,6-tris(benzyloxy)-3-methoxytetrahydro-2H-pyran-2-yl]methanol		C₂₈H₃₂O₆	详情	详情
(X)	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
(XI)	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

Extended Information