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【结 构 式】 
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【分子编号】38198 【品名】(7R,8R,9R,10R)-7-[(3-ethanimidoyl-4-hydroxy-8-methyl-2-oxo-2H-chromen-7-yl)oxy]-10-methoxy-8-(tetrahydro-2H-pyran-2-yloxy)-6-oxaspiro[4.5]dec-9-yl 2-propynyloxycarbamate 【CA登记号】 |
【 分 子 式 】C32H40N2O12 【 分 子 量 】644.67588 【元素组成】C 59.62% H 6.25% N 4.35% O 29.78% |
合成路线1
该中间体在本合成路线中的序号：(XVIII)Acylation of (XII) with acetic anhydride and DMAP yielded the 3-acetyl coumarin (XIII). Following desilylation of (XIII) with tetrabutylammonium fluoride to give (XIV), condensation with O-methyl hydroxylamine gave oxime (XV). Treatment of (XV) with p-nitrophenyl chloroformate and DMAP generated carbonate (XVI), which was further coupled with O-propargyl hydroxylamine (XVII) to yield carbamate (XVIII). The tetrahydropyranyl group of (XVIII) was finally deprotected by methanolysis in the presence of p-toluenesulfonic acid.
| 【1】 Periers, A.-M.; Laurin, P.; Klich, M.; Musicki, B.; Haesslein, J.-L. (Aventis Pharma SA); Novel aromatic amides, preparation method and application as medicines. FR 2773369; WO 9935155 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 16605 | 4-Nitrophenyl chloroformate; 1-[(Chlorocarbonyl)oxy]-4-nitrobenzene | 7693-46-1 | C7H4ClNO4 | 详情 | 详情 | |
| (XII) | 38192 | 4-hydroxy-7-([(7R,8R,9R,10R)-10-methoxy-8-(tetrahydro-2H-pyran-2-yloxy)-9-[(triethylsilyl)oxy]-6-oxaspiro[4.5]dec-7-yl]oxy)-8-methyl-2H-chromen-2-one | C31H46O9Si | 详情 | 详情 | |
| (XIII) | 38193 | 3-acetyl-4-hydroxy-7-([(7R,8R,9R,10R)-10-methoxy-8-(tetrahydro-2H-pyran-2-yloxy)-9-[(triethylsilyl)oxy]-6-oxaspiro[4.5]dec-7-yl]oxy)-8-methyl-2H-chromen-2-one | C33H48O10Si | 详情 | 详情 | |
| (XIV) | 38194 | 3-acetyl-4-hydroxy-7-[[(7R,8R,9R,10R)-9-hydroxy-10-methoxy-8-(tetrahydro-2H-pyran-2-yloxy)-6-oxaspiro[4.5]dec-7-yl]oxy]-8-methyl-2H-chromen-2-one | C27H34O10 | 详情 | 详情 | |
| (XV) | 38195 | 3-ethanimidoyl-4-hydroxy-7-[[(7R,8R,9R,10R)-9-hydroxy-10-methoxy-8-(tetrahydro-2H-pyran-2-yloxy)-6-oxaspiro[4.5]dec-7-yl]oxy]-8-methyl-2H-chromen-2-one | C28H37NO10 | 详情 | 详情 | |
| (XVI) | 38196 | (7R,8R,9R,10R)-7-[(3-ethanimidoyl-4-hydroxy-8-methyl-2-oxo-2H-chromen-7-yl)oxy]-10-methoxy-8-(tetrahydro-2H-pyran-2-yloxy)-6-oxaspiro[4.5]dec-9-yl 4-nitrophenyl carbonate | C35H40N2O14 | 详情 | 详情 | |
| (XVII) | 38197 | O-(2-propynyl)hydroxylamine; 3-(aminooxy)-1-propyne | C3H5NO | 详情 | 详情 | |
| (XVIII) | 38198 | (7R,8R,9R,10R)-7-[(3-ethanimidoyl-4-hydroxy-8-methyl-2-oxo-2H-chromen-7-yl)oxy]-10-methoxy-8-(tetrahydro-2H-pyran-2-yloxy)-6-oxaspiro[4.5]dec-9-yl 2-propynyloxycarbamate | C32H40N2O12 | 详情 | 详情 |