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【结 构 式】 
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【分子编号】45390 【品名】benzyl ((1S,2S,3S,5R)-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-6-oxabicyclo[3.1.0]hex-2-yl)methyl ether; (1S,2S,3S,5R)-2-[(benzyloxy)methyl]-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-6-oxabicyclo[3.1.0]hexane 【CA登记号】 |
【 分 子 式 】C16H22O3S 【 分 子 量 】294.41488 【元素组成】C 65.27% H 7.53% O 16.3% S 10.89% |
合成路线1
该中间体在本合成路线中的序号：(II)The reaction of the chiral epoxy-alcohol (I) with MsCl, TEA and DMAP gives the mesylate (II), which is treated with TBAF in THF to yield the unsaturated epoxide (III).The condensation of (III) with diaminopurine (IV) by means of NaH in DMF affords the carbocyclic purine (V), which is dehydroxylated by reaction with phenyl chlorothioformate, followed by a thermal elimination reaction with Bu3SnH and AIBN to provide the carbocyclic purine (VI). The debenzylation of (VI) by means of BF3/Et2O and Ac2O gives the diacetyl derivative (VII), which is selectively O-deacetylated with NH3 in methanol, yielding 2-acetamido-6-aminopurine (VIII). The reaction of (VIII) with NaNO2 and acetic acid affords the N-acetylated guanine derivative (IX), which is finally treated with NH3 in methanol to provide the target compound.
| 【1】 Jones, M.F.; et al.; Total synthesis of (-)-carbovir. J Chem Soc - Perkins Trans I 1991, 10, 2479. |
| 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) | 29889 | (1S,2R,3S,5R)-2-[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexan-3-ol | C13H16O3 | 详情 | 详情 | |
| (II) | 45390 | benzyl ((1S,2S,3S,5R)-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-6-oxabicyclo[3.1.0]hex-2-yl)methyl ether; (1S,2S,3S,5R)-2-[(benzyloxy)methyl]-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-6-oxabicyclo[3.1.0]hexane | C16H22O3S | 详情 | 详情 | |
| (III) | 45384 | benzyl (1S,2S,5R)-6-oxabicyclo[3.1.0]hex-3-en-2-ylmethyl ether; (1R,4S,5S)-4-[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hex-2-ene | C13H14O2 | 详情 | 详情 | |
| (IV) | 11644 | 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine | 10310-21-1 | C5H4ClN5 | 详情 | 详情 |
| (V) | 45385 | (1S,2S,5S)-2-[(benzyloxy)methyl]-5-(2,6-diamino-9H-purin-9-yl)-3-cyclopenten-1-ol | C18H20N6O2 | 详情 | 详情 | |
| (VI) | 45386 | 2-amino-9-[(1R,4S)-4-[(benzyloxy)methyl]-2-cyclopenten-1-yl]-9H-purin-6-ylamine; 9-[(1R,4S)-4-[(benzyloxy)methyl]-2-cyclopenten-1-yl]-9H-purine-2,6-diamine | C18H20N6O | 详情 | 详情 | |
| (VII) | 45387 | [(1S,4R)-4-[2-(acetamido)-6-amino-9H-purin-9-yl]-2-cyclopenten-1-yl]methyl acetate | C15H18N6O3 | 详情 | 详情 | |
| (VIII) | 45388 | N-[6-amino-9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-9H-purin-2-yl]acetamide | C13H16N6O2 | 详情 | 详情 | |
| (IX) | 45389 | N-[9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl]acetamide | C13H15N5O3 | 详情 | 详情 |