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【结 构 式】 
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【分子编号】37779 【品名】2-(acetamido)-9-[(1R,4S)-4-[(S)-nitro(phenylsulfonyl)methyl]-2-cyclopenten-1-yl]-9H-purin-6-yl diphenylcarbamate 【CA登记号】 |
【 分 子 式 】C32H27N7O7S 【 分 子 量 】653.67536 【元素组成】C 58.8% H 4.16% N 15% O 17.13% S 4.91% |
合成路线1
该中间体在本合成路线中的序号：(V)The enantiocontrolled condensation of the protected guanine (I) with cis-1,3-bis(benzoyloxy)-4-cyclopentene (II) catalyzed by a chiral Pd catalyst gives the alkylated guanine (III), which is condensed with the nitrosulfone (IV) by means of PPh3 and TEA to yield the intermediate (V). The oxidation of (V) with oxone, tetramethylguanidine, and Na2CO3 in methanol/dichloromethane affords the cyclopentenecarboxylate (VI), which is finally reduced with calcium borohydride and deprotected with ammonia to provide the target compound.
| 【1】 Madsen, R.; Brown, B.; Guile, S.D.; Trost, B.M.; Palladium-catalyzed enantioselective synthesis of carbanucleosides. J Am Chem Soc 2000, 122, 25, 5947. |
| 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) | 37775 | 2-(acetamido)-9H-purin-6-yl diphenylcarbamate | C20H16N6O3 | 详情 | 详情 | |
| (II) | 37776 | (1R,4S)-4-(benzoyloxy)-2-cyclopenten-1-yl benzoate | C19H16O4 | 详情 | 详情 | |
| (III) | 37777 | (1S,4R)-4-(2-(acetamido)-6-[[(diphenylamino)carbonyl]oxy]-9H-purin-9-yl)-2-cyclopenten-1-yl benzoate | C32H26N6O5 | 详情 | 详情 | |
| (IV) | 37778 | (nitromethyl)(dioxo)phenyl-lambda(6)-sulfane; nitromethyl phenyl sulfone | 21272-85-5 | C7H7NO4S | 详情 | 详情 |
| (V) | 37779 | 2-(acetamido)-9-[(1R,4S)-4-[(S)-nitro(phenylsulfonyl)methyl]-2-cyclopenten-1-yl]-9H-purin-6-yl diphenylcarbamate | C32H27N7O7S | 详情 | 详情 | |
| (VI) | 37780 | methyl (1S,4R)-4-(2-(acetamido)-6-[[(diphenylamino)carbonyl]oxy]-9H-purin-9-yl)-2-cyclopentene-1-carboxylate | C27H24N6O5 | 详情 | 详情 |