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【结 构 式】 
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【分子编号】36767 【品名】(1R,3S)-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3-fluorocyclopentanol 【CA登记号】 |
【 分 子 式 】C12H25FO2Si 【 分 子 量 】248.4132032 【元素组成】C 58.02% H 10.14% F 7.65% O 12.88% Si 11.31% |
合成路线1
该中间体在本合成路线中的序号：(XVI)Hydrolysis of (XIIIa-b) to the carboxylic acid (XIVa-b), and further iodo decarboxylation yielded a mixture of epimeric iodides (XVa-b). From hydrolysis of the iodide group of (XVa-b) with NaHCO3 only the alpha-alcohol (XVI) was isolated. This was condensed with 6-chloropurine (XVII) under Mitsunobu conditions to give adduct (XVIII). The 6-chloro derivative (XVIII) was converted into the protected adenosine analogue (XIX) by treatment with methanolic ammonia in a steel bomb at 100 C. Finally, desilylation of (XIX) employing tetrabutylammonium fluoride furnished the title compound.
| 【1】 Gumina, G.; et al.; Stereoselective synthesis of carbocyclic L-4'-fluoro-2',3'-dideoxyadenosine. Org Lett 2000, 2, 9, 1229. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIIIa) | 36757 | ethyl (1S,3S)-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3-fluorocyclopentanecarboxylate | C15H29FO3Si | 详情 | 详情 | |
| (XIIIb) | 36758 | ethyl (1R,3S)-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3-fluorocyclopentanecarboxylate | C15H29FO3Si | 详情 | 详情 | |
| (XIVa) | 36763 | (1S,3S)-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3-fluorocyclopentanecarboxylic acid | C13H25FO3Si | 详情 | 详情 | |
| (XIVb) | 36764 | (1R,3S)-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3-fluorocyclopentanecarboxylic acid | C13H25FO3Si | 详情 | 详情 | |
| (XVa) | 36765 | tert-butyl[[(1S,3S)-1-fluoro-3-iodocyclopentyl]methoxy]dimethylsilane; tert-butyl(dimethyl)silyl [(1S,3S)-1-fluoro-3-iodocyclopentyl]methyl ether | C12H24FIOSi | 详情 | 详情 | |
| (XVb) | 36766 | tert-butyl[[(1S,3R)-1-fluoro-3-iodocyclopentyl]methoxy]dimethylsilane; tert-butyl(dimethyl)silyl [(1S,3R)-1-fluoro-3-iodocyclopentyl]methyl ether | C12H24FIOSi | 详情 | 详情 | |
| (XVI) | 36767 | (1R,3S)-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3-fluorocyclopentanol | C12H25FO2Si | 详情 | 详情 | |
| (XVII) | 17692 | 6-Chloropurine; 6-chloro-9H-purine | 87-42-3 | C5H3ClN4 | 详情 | 详情 |
| (XVIII) | 36768 | 9-[(1S,3S)-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3-fluorocyclopentyl]-6-chloro-9H-purine; tert-butyl(dimethyl)silyl [(1S,3S)-3-(6-chloro-9H-purin-9-yl)-1-fluorocyclopentyl]methyl ether | C17H26ClFN4OSi | 详情 | 详情 | |
| (XIX) | 36769 | 9-[(1S,3S)-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3-fluorocyclopentyl]-9H-purin-6-amine; 9-[(1S,3S)-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3-fluorocyclopentyl]-9H-purin-6-ylamine | C17H28FN5OSi | 详情 | 详情 |