【结 构 式】 |
【分子编号】33830 【品名】methyl 1-[(2R,3R,4R,5R)-3,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-2-furanyl]-1H-1,2,4-triazole-3-carboxylate 【CA登记号】 |
【 分 子 式 】C30H25N3O9 【 分 子 量 】571.54332 【元素组成】C 63.05% H 4.41% N 7.35% O 25.19% |
合成路线1
该中间体在本合成路线中的序号:(XI)The condensation of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (X) with 1,2,4-triazole-3-carboxylic acid methyl ester (VII) by means of PNPP at 160 C C gives 1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (XI), which is finally treated with NH4OH in methanol.
【1】 Witkowski, J.T.; et al.; Design, synthesis, and broad spectrum antiviral activity of 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide and related nucleosides. J Med Chem 1972, 15, 11, 1150. |
【2】 Laguna, N; Robins, R.K.; Witkowski, J.T. (ICN Pharmaceuticals, Inc.); 1,2,4-Triazole nucleosides. DE 2220246; US 3798209 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VII) | 33827 | methyl 1H-1,2,4-triazole-3-carboxylate | 4928-88-5 | C4H5N3O2 | 详情 | 详情 |
(X) | 26984 | (2R,3R,4R,5S)-5-(acetoxy)-4-(benzoyloxy)-2-[(benzoyloxy)methyl]tetrahydro-3-furanyl benzoate | C28H24O9 | 详情 | 详情 | |
(XI) | 33830 | methyl 1-[(2R,3R,4R,5R)-3,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-2-furanyl]-1H-1,2,4-triazole-3-carboxylate | C30H25N3O9 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(XI)The silylation of 1,2,4-triazole-3-carboxylic acid methyl ester (VII) with hexamethyldisylazane (HMDS) gives 1-(trimethylsilyl)-1,2,4-triazole-3-carboxylic acid methyl ester (XII), which is condensed with 2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl bromide (XIII) by means of PNPP at 160 C to afford the previously described intermediate 1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (XI).
【1】 Laguna, N; Robins, R.K.; Witkowski, J.T. (ICN Pharmaceuticals, Inc.); 1,2,4-Triazole nucleosides. DE 2220246; US 3798209 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VII) | 33827 | methyl 1H-1,2,4-triazole-3-carboxylate | 4928-88-5 | C4H5N3O2 | 详情 | 详情 |
(XI) | 33830 | methyl 1-[(2R,3R,4R,5R)-3,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-2-furanyl]-1H-1,2,4-triazole-3-carboxylate | C30H25N3O9 | 详情 | 详情 | |
(XII) | 33831 | methyl 1-(trimethylsilyl)-1H-1,2,4-triazole-3-carboxylate | C7H13N3O2Si | 详情 | 详情 | |
(XIII) | 33832 | [(2R,3S,4R)-3,4-bis(benzoyloxy)-5-bromotetrahydro-2-furanyl]methyl benzoate | C26H21BrO7 | 详情 | 详情 |