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【结 构 式】 
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【药物名称】 【化学名称】(3beta,5alpha,25R)-3-[4-O-[4,6-O-Bis[N-(2-fluorophenyl)carbamoyl]-beta-D-glucopyranosyl]-beta-D-glucopyranosyloxy]spirostan-12-one 【CA登记号】171267-34-8 【 分 子 式 】C53H70F2N2O16 【 分 子 量 】1029.14945 |
【开发单位】Pfizer (Originator) 【药理作用】Lipoprotein Disorders, Treatment of , METABOLIC DRUGS, Cholesterol Absorption Inhibitors |
合成路线1
The acetalization of Hecogenyl beta-O-cellobioside (I) with 4-methoxybenzaldehyde diethyl acetal (II) by means of pyridinium tosylate in THF gives the acetal (III), which is acylated with 2-methoxyacetyl chloride (IV) by means of pyridine and DMAP in dichloromethane yielding the pentaacetate (V). The elimination of the acetal group of (V) with H2 over Pd/C in ethyl acetate affords the dihydroxy compound (VI).
| 【1】 Urban, F.J.; et al.; Process research and large-scale synthesis of 4'',6''-bis((2-fluorophenyl)carbomoyl)hecogenyl beta-O-cellobioside: A potent cholesterol absorption inhibitor. Org Process Res Dev 1998, 2, 2, 66. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35669 | Pamaqueside | 150332-35-7 | C39H62O14 | 详情 | 详情 |
| (II) | 35670 | 1-(diethoxymethyl)-4-methoxybenzene; 4-(diethoxymethyl)phenyl methyl ether | C12H18O3 | 详情 | 详情 | |
| (III) | 35671 | C47H68O15 | 详情 | 详情 | ||
| (IV) | 13429 | 2-Methoxyacetyl chloride; Methoxyacetyl chloride | 38870-89-2 | C3H5ClO2 | 详情 | 详情 |
| (V) | 35672 | C62H88O25 | 详情 | 详情 | ||
| (VI) | 35673 | C54H82O24 | 详情 | 详情 |
合成路线2
Intermediate (VI) is treated with 2-fluorophenyl isocyanate (VII) and CuCl in DMF to give the bis carbamate (VIII). Finally, this compound is deacetylated with NH4OH in THF.
| 【1】 Urban, F.J.; et al.; Process research and large-scale synthesis of 4'',6''-bis((2-fluorophenyl)carbomoyl)hecogenyl beta-O-cellobioside: A potent cholesterol absorption inhibitor. Org Process Res Dev 1998, 2, 2, 66. |