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【结 构 式】 
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【分子编号】64184 【品名】(2R,3S,4R,5R)-5-azido-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3-ol 【CA登记号】 |
【 分 子 式 】C22H45N3O5Si 【 分 子 量 】459.70202 【元素组成】C 57.48% H 9.87% N 9.14% O 17.4% Si 6.11% |
合成路线1
该中间体在本合成路线中的序号：(LIII)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).
| 【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 | CAS号 | 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 |