allyl (2R,3S,4R,5R)-5-azido-6-{[tert-butyl(dimethyl)silyl]oxy}-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(decyloxy)tetrahydro-2H-pyran-3-yl carbonate -Drug Synthesis Database

【结构式】

【分子编号】64186

【品名】allyl (2R,3S,4R,5R)-5-azido-6-{[tert-butyl(dimethyl)silyl]oxy}-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(decyloxy)tetrahydro-2H-pyran-3-yl carbonate

【CA登记号】

【分子式】C₃₂H₆₃N₃O₇Si₂

【分子量】658.03924

【元素组成】C 58.41% H 9.65% N 6.39% O 17.02% Si 8.54%

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：(LV)

Alkylation of azido sugar (XLIV) with 1-iododecane (LI) in the presence of Ag2O provided decyl ether (LII). Then, selective acetonide hydrolysis in (LII) to (LIII), followed by silylation with tert-butyldimethylsilyl chloride provided the bis-silyl ether (LIV). Alcohol (LIV) was then protected as the allyl carbonate (LV) by treatment with phosgene, followed by allyl alcohol. The primary silyl ether group of (LV) was selectively removed by treatment with HF giving the monosaccharide (LVI), which was coupled with imidate (XXXIV) yielding disaccharide (LVII).

参考文献中间体

合成目标

【1】 Kobayashi, S.; Kawata, T.; Christ, W.J.; Rossignol, D.P. (Eisai Co., Ltd.); Substd. liposaccharides useful in the treatment and prevention of endotoxemia. US 5750664; WO 9639411 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXXIV)	64166	(3R,4R,5S,6R)-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-{[(2,2,2-trichloroethoxy)carbonyl]amino}tetrahydro-2H-pyran-2-yl 2,2,2-trichloroethanimidoate	C₂₉H₄₇Cl₆N₂O₁₁P	详情	详情
(XLIV)	59080	(4aR,6S,7R,8R,8aS)-7-azido-6-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-ol	C₁₅H₂₉N₃O₅Si	详情	详情
(LI)	64182	1-iododecane	C₁₀H₂₁I	详情	详情
(LII)	64183	{[(4aR,7R,8R,8aS)-7-azido-8-(decyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy}(tert-butyl)dimethylsilane; (4aR,7R,8R,8aS)-7-azido-6-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl decyl ether	C₂₅H₄₉N₃O₅Si	详情	详情
(LIII)	64184	(2R,3S,4R,5R)-5-azido-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3-ol	C₂₂H₄₅N₃O₅Si	详情	详情
(LIV)	64185	(2R,3S,4R,5R)-5-azido-6-{[tert-butyl(dimethyl)silyl]oxy}-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(decyloxy)tetrahydro-2H-pyran-3-ol	C₂₈H₅₉N₃O₅Si₂	详情	详情
(LV)	64186	allyl (2R,3S,4R,5R)-5-azido-6-{[tert-butyl(dimethyl)silyl]oxy}-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(decyloxy)tetrahydro-2H-pyran-3-yl carbonate	C₃₂H₆₃N₃O₇Si₂	详情	详情
(LVI)	64187	allyl (2R,3S,4R,5R)-5-azido-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl carbonate	C₂₆H₄₉N₃O₇Si	详情	详情
(LVII)	64188	allyl (2R,3S,4R,5R)-5-azido-2-{[((2R,3R,4R,5S,6R)-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-{[(2,2,2-trichloroethoxy)carbonyl]amino}tetrahydro-2H-pyran-2-yl)oxy]methyl}-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)tetrahydro-2H-pyran-3-yl carbonate	C₅₃H₉₄Cl₃N₄O₁₇PSi	详情	详情

Extended Information