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【结 构 式】 
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【分子编号】39771 【品名】(1R)-1-(2-chloro-2-oxoethyl)dodecyl myristate 【CA登记号】 |
【 分 子 式 】C28H53ClO3 【 分 子 量 】473.17972 【元素组成】C 71.07% H 11.29% Cl 7.49% O 10.14% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Protection of the amino group of aminopyranoside (VI) with 2,2,2-trichloroethyl chloroformate under Schotten-Baumann conditions afforded trichloroethyl carbamate (VII). Subsequent O-acylation of (VII) with acid chloride (VIII) gave ester (IX). Acetonide (IX) cleavage with aqueous AcOH yielded diol (X), which was protected at the primary hydroxyl group using 1,1-dimethyl-2,2,2-trichloroethyl chloroformate yielding (XI). Conversion of (XI) to the required phosphate (XII) was effected by reaction with diphenyl chlorophosphate. The intermediate glycosyl chloride (XIII) was then obtained by treatment of (XII) with dichloromethyl methyl ether and ZnCl2.
| 【1】 Sowell, C.G.; Weber, P.A.; Elliott, G.T. (Corixa Corp.); Phosphoglycolipid and methods for its use. WO 0011010 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 39769 | (4aR,6R,7R,8R,8aS)-7-amino-2,2-dimethyl-6-[2-(trimethylsilyl)ethoxy]hexahydropyrano[3,2-d][1,3]dioxin-8-ol | C14H29NO5Si | 详情 | 详情 | |
| (VII) | 39770 | 2,2,2-trichloroethyl (4aR,6R,7R,8R,8aS)-8-hydroxy-2,2-dimethyl-6-[2-(trimethylsilyl)ethoxy]hexahydropyrano[3,2-d][1,3]dioxin-7-ylcarbamate | C17H30Cl3NO7Si | 详情 | 详情 | |
| (VIII) | 39771 | (1R)-1-(2-chloro-2-oxoethyl)dodecyl myristate | C28H53ClO3 | 详情 | 详情 | |
| (IX) | 39772 | (4aR,6R,7R,8R,8aR)-2,2-dimethyl-7-[[(2,2,2-trichloroethoxy)carbonyl]amino]-6-[2-(trimethylsilyl)ethoxy]hexahydropyrano[3,2-d][1,3]dioxin-8-yl (3R)-3-(tetradecanoyloxy)tetradecanoate | C45H82Cl3NO10Si | 详情 | 详情 | |
| (X) | 39773 | (2R,3R,4R,5R,6R)-3-hydroxy-2-(hydroxymethyl)-5-[[(2,2,2-trichloroethoxy)carbonyl]amino]-6-[2-(trimethylsilyl)ethoxy]tetrahydro-2H-pyran-4-yl (3R)-3-(tetradecanoyloxy)tetradecanoate | C42H78Cl3NO10Si | 详情 | 详情 | |
| (XI) | 39774 | (2R,3R,4R,5R,6R)-3-hydroxy-2-([[(2,2,2-trichloro-1,1-dimethylethoxy)carbonyl]oxy]methyl)-5-[[(2,2,2-trichloroethoxy)carbonyl]amino]-6-[2-(trimethylsilyl)ethoxy]tetrahydro-2H-pyran-4-yl (3R)-3-(tetradecanoyloxy)tetradecanoate | C47H83Cl6NO12Si | 详情 | 详情 | |
| (XII) | 39775 | (2R,3R,4R,5R,6R)-3-[(diphenoxyphosphoryl)oxy]-2-([[(2,2,2-trichloro-1,1-dimethylethoxy)carbonyl]oxy]methyl)-5-[[(2,2,2-trichloroethoxy)carbonyl]amino]-6-[2-(trimethylsilyl)ethoxy]tetrahydro-2H-pyran-4-yl (3R)-3-(tetradecanoyloxy)tetradecanoate | C59H92Cl6NO15PSi | 详情 | 详情 | |
| (XIII) | 39776 | (2R,3R,4R,5S,6R)-2-chloro-5-[(diphenoxyphosphoryl)oxy]-3-[(ethoxycarbonyl)amino]-6-([[(2,2,2-trichloro-1,1-dimethylethoxy)carbonyl]oxy]methyl)tetrahydro-2H-pyran-4-yl (3R)-3-(tetradecanoyloxy)tetradecanoate | C54H82Cl4NO14P | 详情 | 详情 |