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【结 构 式】 
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【分子编号】17713 【品名】(2S,3R,4S,5R)-2-methoxy-5-[[(4-methoxybenzyl)oxy]methyl]-4-[(methylsulfonyl)oxy]tetrahydro-3-furanyl methanesulfonate 【CA登记号】 |
【 分 子 式 】C16H24O10S2 【 分 子 量 】440.49256 【元素组成】C 43.63% H 5.49% O 36.32% S 14.56% |
合成路线1
该中间体在本合成路线中的序号：(XXX)The treatment of 2,3-O-dimesyl-5-O-(4-methoxybenzyl)-1-O-methyl-alpha-D-xylofuranose (XXX) with NaBH4 gives 3-deoxy-5-O-(4-methoxybenzyl)-1-O-methyl-alpha-D-xylofuranose (XXXI), which is fluorinated with diethylamido sulfur trifluoride as before, yielding 2,3-dideoxy-2-fluoro-5-O-(4-methoxybenzyl)-alpha-D-arabinofuranose (XXXII). The condensation of (XXXII) with adenine (XXXIII) by means of acetyl bromide affords 9-[2,3-dideoxy-2-fluoro-5-O-(4-methoxybenzyl)-beta-D-arabinofuraosyl]adenine (XXXIV), which is finally deprotected by hydrogenation over Pd/C in ethanol.
| 【1】 Castaner, J.; Graul, A.; Silvestre, J.S.; Lodenosine. Drugs Fut 1998, 23, 11, 1176-1189. |
| 【2】 Stadelmann, B.; alpha-D-Pentofuranoside derivs., process for preparing the same and their use. WO 9606103 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXX) | 17713 | (2S,3R,4S,5R)-2-methoxy-5-[[(4-methoxybenzyl)oxy]methyl]-4-[(methylsulfonyl)oxy]tetrahydro-3-furanyl methanesulfonate | C16H24O10S2 | 详情 | 详情 | |
| (XXXI) | 17714 | (2S,3R,5S)-2-methoxy-5-[[(4-methoxybenzyl)oxy]methyl]tetrahydro-3-furanol | C14H20O5 | 详情 | 详情 | |
| (XXXII) | 17715 | (2S,3S,5S)-3-fluoro-5-[[(4-methoxybenzyl)oxy]methyl]tetrahydro-2-furanyl methyl ether; (2S,3S,5S)-3-fluoro-2-methoxy-5-[[(4-methoxybenzyl)oxy]methyl]tetrahydrofuran | C14H19FO4 | 详情 | 详情 | |
| (XXXIII) | 10343 | 9H-Purin-6-amine; 9H-Purin-6-ylamine; Adenine | 73-24-5 | C5H5N5 | 详情 | 详情 |
| (XXXIV) | 17717 | 9-((2R,3S,5S)-3-fluoro-5-[[(4-methoxybenzyl)oxy]methyl]tetrahydro-2-furanyl)-9H-purin-6-amine; 9-((2R,3S,5S)-3-fluoro-5-[[(4-methoxybenzyl)oxy]methyl]tetrahydro-2-furanyl)-9H-purin-6-ylamine | C18H20FN5O3 | 详情 | 详情 |