(2S,3R,4R,5R)-2-[[(2S,3R,4S,5S)-3-(acetoxy)-2-(benzyloxy)-5-hydroxytetrahydro-2H-pyran-4-yl]oxy]-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate -Drug Synthesis Database

【结构式】

【分子编号】48976

【品名】(2S,3R,4R,5R)-2-[[(2S,3R,4S,5S)-3-(acetoxy)-2-(benzyloxy)-5-hydroxytetrahydro-2H-pyran-4-yl]oxy]-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate

【CA登记号】

【分子式】C₃₉H₆₀O₁₂Si₂

【分子量】777.0692

【元素组成】C 60.28% H 7.78% O 24.71% Si 7.23%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XIV)

Synthesis of intermediate disaccharide (XVII): The regioselective glycosylation of intermediate arabinose derivative (VI) with the intermediate acetimidate (XIII) by means of BF3/Et2O gives the disaccharide (XIV), which is silylated with Tes-OTf and lutidine in dichloromethane to yield the fully protected disaccharide (XV). Elimination of the benzyl protecting group of (XV) by hydrogenation with H2 over Pd/C in hot ethyl acetate affords the hemiacetal (XVI), which is converted into the target trichloroacetimidate (XVII) by reaction with trichloroacetonitrile and DBU in dichloromethane.

参考文献中间体

合成目标

【1】 Deng, S.; et al.; First total synthesis of an exceptionally potent antitumor saponin, OSW-1. J Org Chem 1999, 64, 1, 202.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VI)	48969	(2S,3R,4S,5S)-2-(benzyloxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yl acetate	C₁₄H₁₈O₆	详情	详情
(XIII)	48975	(3R,4R,5R)-2-[(2,2,2-trichloroethanimidoyl)oxy]-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₂₇H₄₄Cl₃NO₇Si₂	详情	详情
(XIV)	48976	(2S,3R,4R,5R)-2-[[(2S,3R,4S,5S)-3-(acetoxy)-2-(benzyloxy)-5-hydroxytetrahydro-2H-pyran-4-yl]oxy]-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₃₉H₆₀O₁₂Si₂	详情	详情
(XV)	48977	(2S,3R,4R,5R)-2-([(2S,3R,4R,5S)-3-(acetoxy)-2-(benzyloxy)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₄₅H₇₄O₁₂Si₃	详情	详情
(XVI)	48978	(2S,3R,4R,5R)-2-([(3R,4R,5S)-3-(acetoxy)-2-hydroxy-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₃₈H₆₈O₁₂Si₃	详情	详情
(XVII)	48979	(2S,3R,4R,5R)-2-([(3R,4R,5S)-3-(acetoxy)-2-[(2,2,2-trichloroethanimidoyl)oxy]-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₄₀H₆₈Cl₃NO₁₂Si₃	详情	详情

Extended Information