methyl 1-(trimethylsilyl)-1H-1,2,4-triazole-3-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】33831

【品名】methyl 1-(trimethylsilyl)-1H-1,2,4-triazole-3-carboxylate

【CA登记号】

【分子式】C₇H₁₃N₃O₂Si

【分子量】199.28474

【元素组成】C 42.19% H 6.58% N 21.09% O 16.06% Si 14.09%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XII)

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).

参考文献中间体

合成目标

【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

合成路线2

该中间体在本合成路线中的序号：(XII)

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).

参考文献中间体

合成目标

【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