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【结 构 式】

【分子编号】33834

【品名】methyl 1-[(2R,3R,4S,5R)-4-(acetoxy)-5-[(acetoxy)methyl]-3-hydroxytetrahydro-2-furanyl]-1H-1,2,4-triazole-3-carboxylate

【CA登记号】

【 分 子 式 】C13H17N3O8

【 分 子 量 】343.2934

【元素组成】C 45.48% H 4.99% N 12.24% O 37.28%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XV)

The condensation of 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose (XIV) with 1,2,4-triazole-3-carboxylic acid methyl ester (VII) by means of PNPP at 160 C gives 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (XV), which is finally treated with NH4OH in methanol. The condensation of 2,3,5-tri-O-acetyl-beta-D-ribofuranosyl bromide (XVI) with 1-(trimethylsilyl)-1,2,4-triazole-3-carboxylic acid methyl ester (XII) in acetonitrile gives the previously reported intermediate 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (XV).

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
(XII) 33831 methyl 1-(trimethylsilyl)-1H-1,2,4-triazole-3-carboxylate C7H13N3O2Si 详情 详情
(XIV) 33835 (2R,3R,4R,5S)-4,5-bis(acetoxy)-2-[(acetoxy)methyl]tetrahydro-3-furanyl acetate 13035-61-5 C13H18O9 详情 详情
(XV) 33834 methyl 1-[(2R,3R,4S,5R)-4-(acetoxy)-5-[(acetoxy)methyl]-3-hydroxytetrahydro-2-furanyl]-1H-1,2,4-triazole-3-carboxylate C13H17N3O8 详情 详情
(XVI) 33833 (2R,3S,4R,5S)-4-(acetoxy)-2-[(acetoxy)methyl]-5-bromotetrahydro-3-furanyl acetate C11H15BrO7 详情 详情
Extended Information