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【结 构 式】 
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【分子编号】53164 【品名】methyl 3-[({[(2R,3R,4R,5R,6R)-3-(acetylamino)-5-(acetyloxy)-6-[(acetyloxy)methyl]-2-(phosphonooxy)tetrahydro-2H-pyran-4-yl]oxy}methyl)(ethoxy)phosphoryl]-2-methylpropanoate 【CA登记号】n/a |
【 分 子 式 】C20H35NO15P2 【 分 子 量 】591.443164 【元素组成】C 40.62% H 5.96% N 2.37% O 40.58% P 10.47% |
合成路线1
该中间体在本合成路线中的序号：(XII)Treatment of (X) with BuLi and diphenyl chlorophosphate led to stereoselective formation of the alpha phosphate ester (XI). The phenyl phosphate ester groups of (XI) were then deprotected by catalytic hydrogenation over PtO2 to afford (XII), isolated as a mixture of two major diastereomers. Coupling of (XII) with uridine monophosphate morpholidate (XIII) led to the uridine diphosphate-containing derivative (XIV). Finally, saponification of the ester groups of (XIV) with aqueous NaOH furnished the title compound.
| 【1】 Reck, F.; et al.; Inhibitors of the bacterial cell wall biosynthesis enzyme MurC. Bioorg Med Chem Lett 2001, 11, 11, 1451. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 53162 | methyl 3-[[({(3R,4R,5R,6R)-3-(acetylamino)-5-(acetyloxy)-6-[(acetyloxy)methyl]-2-hydroxytetrahydro-2H-pyran-4-yl}oxy)methyl](ethoxy)phosphoryl]-2-methylpropanoate | n/a | C20H34NO12P | 详情 | 详情 |
| (XI) | 53163 | methyl 3-[[({(2R,3R,4R,5R,6R)-3-(acetylamino)-5-(acetyloxy)-6-[(acetyloxy)methyl]-2-[(diphenoxyphosphoryl)oxy]tetrahydro-2H-pyran-4-yl}oxy)methyl](ethoxy)phosphoryl]-2-methylpropanoate | n/a | C32H43NO15P2 | 详情 | 详情 |
| (XII) | 53164 | methyl 3-[({[(2R,3R,4R,5R,6R)-3-(acetylamino)-5-(acetyloxy)-6-[(acetyloxy)methyl]-2-(phosphonooxy)tetrahydro-2H-pyran-4-yl]oxy}methyl)(ethoxy)phosphoryl]-2-methylpropanoate | n/a | C20H35NO15P2 | 详情 | 详情 |
| (XIII) | 53165 | {(2R,3S,4R,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl hydrogen 4-morpholinylphosphonate | n/a | C13H20N3O9P | 详情 | 详情 |
| (XIV) | 53166 | n/a | C29H46N3O23P3 | 详情 | 详情 |