benzyl (2R,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6S)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(benzyloxy)-6-({(2R,3S,4R,5R,6R)-6-({(2R,3S,4R,5R,6S)-5-(benzyloxy)-2-[(benzyloxy)methyl]-4,6-dimethoxytetrahydro-2H-pyran-3-yl}oxy)-2-[(benzyloxy)carbonyl]-4,5-dimethoxytetrahydro-2H-pyran-3-yl}oxy)tetrahydro-2H-pyran-3-yl]oxy}-3-hydroxy-4,5-dimethoxytetrahydro-2H-pyran-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】58164

【品名】benzyl (2R,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6S)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(benzyloxy)-6-({(2R,3S,4R,5R,6R)-6-({(2R,3S,4R,5R,6S)-5-(benzyloxy)-2-[(benzyloxy)methyl]-4,6-dimethoxytetrahydro-2H-pyran-3-yl}oxy)-2-[(benzyloxy)carbonyl]-4,5-dimethoxytetrahydro-2H-pyran-3-yl}oxy)tetrahydro-2H-pyran-3-yl]oxy}-3-hydroxy-4,5-dimethoxytetrahydro-2H-pyran-2-carboxylate

【CA登记号】

【分子式】C₆₉H₈₄O₂₅

【分子量】1313.41096

【元素组成】C 63.1% H 6.45% O 30.45%

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：(XXXIV)

Preparation of the tetrasaccharide building block (XXXIV) is carried out as follows. The disaccharide benzoate ester (XXVII) is hydrolyzed to alcohol (XXVIII), which is subsequently alkylated with iodomethane and NaH to the methyl ether (XXIX). Acidic hydrolysis of the acetonide group of (XXIX) provides diol (XXX). The primary alcohol of (XXX) is then oxidized by means of TEMPO and NaOCl, yielding carboxylic acid (XXXI), which is further converted to the benzyl ester (XXXII) upon treatment with benzyl bromide and KHCO3. Coupling of the disaccharide acceptor (XXXII) with imidate (XXXIII) in the presence of tert-butyldimethylsilyl triflate, followed by removal of the levulinate ester with hydrazine acetate, furnishes tetrasaccharide (XXXIV).

参考文献中间体

合成目标

【1】 Petitou, M.; Herbert, J.-M.; Duchaussoy, P.; Basten, J.; Dreef-Tromp, C.; Driguez, P.-A.; Van Boeckel, C. (Akzo Nobel N.V.; Sanofi-Synthélabo); Synthetic polysaccharides, their method of production and pharmaceutical compsns. containing same. EP 1049721; FR 2773804; US 6528497; WO 9936443 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXVII)	58157	(4aS,6R,7R,8S,8aS)-6-({(2R,3S,4R,5R,6S)-5-(benzyloxy)-2-[(benzyloxy)methyl]-4,6-dimethoxytetrahydro-2H-pyran-3-yl}oxy)-8-methoxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate	C₃₉H₄₈O₁₂	详情	详情
(XXVIII)	58158	(4aS,6R,7R,8R,8aS)-6-({(2R,3S,4R,5R,6S)-5-(benzyloxy)-2-[(benzyloxy)methyl]-4,6-dimethoxytetrahydro-2H-pyran-3-yl}oxy)-8-methoxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-ol	C₃₂H₄₄O₁₁	详情	详情
(XXIX)	58159	(4aS,6R,7R,8R,8aS)-6-({(2R,4R,5R,6S)-5-(benzyloxy)-2-[(benzyloxy)methyl]-4,6-dimethoxytetrahydro-2H-pyran-3-yl}oxy)-7-methoxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl methyl ether; (4aS,6R,7R,8R,8aS)-6-({(2R,4R,5R,6S)-5-(benzyloxy)-2-[(benzyloxy)methyl]-4,6-dimethoxytetrahydro-2H-pyran-3-yl}oxy)-7,8-dimethoxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxine	C₃₃H₄₆O₁₁	详情	详情
(XXX)	58160	(2S,3S,4S,5R,6S)-6-({(2R,4R,5R,6S)-5-(benzyloxy)-2-[(benzyloxy)methyl]-4,6-dimethoxytetrahydro-2H-pyran-3-yl}oxy)-2-(hydroxymethyl)-4,5-dimethoxytetrahydro-2H-pyran-3-ol	C₃₀H₄₂O₁₁	详情	详情
(XXXI)	58161	(2R,3S,4S,5R,6R)-6-({(2R,3S,4R,5R,6S)-5-(benzyloxy)-2-[(benzyloxy)methyl]-4,6-dimethoxytetrahydro-2H-pyran-3-yl}oxy)-3-hydroxy-4,5-dimethoxytetrahydro-2H-pyran-2-carboxylic acid	C₃₀H₄₀O₁₂	详情	详情
(XXXII)	58162	benzyl (2R,3S,4S,5R,6R)-6-({(2R,3S,4R,5R,6S)-5-(benzyloxy)-2-[(benzyloxy)methyl]-4,6-dimethoxytetrahydro-2H-pyran-3-yl}oxy)-3-hydroxy-4,5-dimethoxytetrahydro-2H-pyran-2-carboxylate	C₃₇H₄₆O₁₂	详情	详情
(XXXIII)	58163	benzyl (2R,3S,4R,5R,6R)-6-({(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(benzyloxy)-6-[(2,2,2-trichloroethanimidoyl)oxy]tetrahydro-2H-pyran-3-yl}oxy)-4,5-dimethoxy-3-[(4-oxopentanoyl)oxy]tetrahydro-2H-pyran-2-carboxylate	C₃₉H₄₆Cl₃NO₁₆	详情	详情
(XXXIV)	58164	benzyl (2R,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6S)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(benzyloxy)-6-({(2R,3S,4R,5R,6R)-6-({(2R,3S,4R,5R,6S)-5-(benzyloxy)-2-[(benzyloxy)methyl]-4,6-dimethoxytetrahydro-2H-pyran-3-yl}oxy)-2-[(benzyloxy)carbonyl]-4,5-dimethoxytetrahydro-2H-pyran-3-yl}oxy)tetrahydro-2H-pyran-3-yl]oxy}-3-hydroxy-4,5-dimethoxytetrahydro-2H-pyran-2-carboxylate	C₆₉H₈₄O₂₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXXIV)

The nonasaccharide imidate (XXVI) is coupled to the tetrasaccharide acceptor (XXXIV) to provide adduct (XXXV). Subsequent deprotection of the levulinate ester of (XXXV) to afford (XXXVI) is effected by treatment with hydrazine acetate.

参考文献中间体

合成目标

【1】 Petitou, M.; Herbert, J.-M.; Duchaussoy, P.; Basten, J.; Dreef-Tromp, C.; Driguez, P.-A.; Van Boeckel, C. (Akzo Nobel N.V.; Sanofi-Synthélabo); Synthetic polysaccharides, their method of production and pharmaceutical compsns. containing same. EP 1049721; FR 2773804; US 6528497; WO 9936443 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXVI)	58156		C₉₅H₁₅₄Cl₃NO₅₀	详情	详情
(XXXIV)	58164	benzyl (2R,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6S)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(benzyloxy)-6-({(2R,3S,4R,5R,6R)-6-({(2R,3S,4R,5R,6S)-5-(benzyloxy)-2-[(benzyloxy)methyl]-4,6-dimethoxytetrahydro-2H-pyran-3-yl}oxy)-2-[(benzyloxy)carbonyl]-4,5-dimethoxytetrahydro-2H-pyran-3-yl}oxy)tetrahydro-2H-pyran-3-yl]oxy}-3-hydroxy-4,5-dimethoxytetrahydro-2H-pyran-2-carboxylate	C₆₉H₈₄O₂₅	详情	详情
(XXXV)	58165		C₁₆₂H₂₃₆O₇₄	详情	详情
(XXXVI)	58166		C₁₅₇H₂₃₀O₇₂	详情	详情

Extended Information