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【结 构 式】 
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【分子编号】34916 【品名】(2R,3S,4R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-chlorotetrahydro-3-furanyl acetate 【CA登记号】 |
【 分 子 式 】C11H15ClO7 【 分 子 量 】294.6886 【元素组成】C 44.83% H 5.13% Cl 12.03% O 38% |
合成路线1
该中间体在本合成路线中的序号：(V)This compound has been obtained by two similar ways: 1) The condensation of 1-O-acetyl-2,3,5-O-tribenzoyl-beta-D-ribofuranose (I) with N6-benzoyl-9-(trimethylsilyl)adenine (II) by means of trimethylsilyl perchlorate or trimethylsilyl trifluoromethanesulfonate in dichloroethane gives the tetrabenzoyladenosine (III), which is finally debenzoylated with ammonia in methanol. 2) The reaction of tetraacetyl-D-ribofuranose (IV) with dry HCl in ethyl ether gives the 1-chloro derivative (V), which is condensed with the silver salt of 2,8-dichloroadenine (VI) in refluxing xylene yielding the acetylated dichloroadenosine (VII). The hydrolysis of (VII) with ammonia in methanol affords 2,8-dichloroadenosine (VIII), which is finally dechlorinated by hydrogenation with H2 over Pd/BaSO4 in aqueous NaOH.
| 【1】 Davoll, J.; et al.; Experiments on the synthesis of purine nucleosides. Part XIX. A synthesis of adenosine. J Chem Soc 1948, 967. |
| 【2】 Krolikiewicz, K.; Vorbrueggen, H.; New catalysts for the synthesis of nucleosides. Angew Chem. Int Ed Engl 1975, 14, 6, 421. |
| 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) | 26984 | (2R,3R,4R,5S)-5-(acetoxy)-4-(benzoyloxy)-2-[(benzoyloxy)methyl]tetrahydro-3-furanyl benzoate | C28H24O9 | 详情 | 详情 | |
| (II) | 34914 | N-[9-(trimethylsilyl)-9H-purin-6-yl]benzamide | C15H17N5OSi | 详情 | 详情 | |
| (III) | 34915 | (2R,3R,4R,5R)-2-[6-(benzoylamino)-9H-purin-9-yl]-4-(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-3-furanyl benzoate | C38H29N5O8 | 详情 | 详情 | |
| (IV) | 33835 | (2R,3R,4R,5S)-4,5-bis(acetoxy)-2-[(acetoxy)methyl]tetrahydro-3-furanyl acetate | 13035-61-5 | C13H18O9 | 详情 | 详情 |
| (V) | 34916 | (2R,3S,4R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-chlorotetrahydro-3-furanyl acetate | C11H15ClO7 | 详情 | 详情 | |
| (VI) | 34917 | C5H2AgCl2N5 | 详情 | 详情 | ||
| (VII) | 34918 | (2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-(6-amino-2,8-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate | C16H17Cl2N5O7 | 详情 | 详情 | |
| (VIII) | 34919 | (2R,3R,4S,5R)-2-(6-amino-2,8-dichloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol | C10H11Cl2N5O4 | 详情 | 详情 |