以2’,3’-异丙叉利巴韦林(Ⅰ)为原料,通过碱催化与3个不同的酰氯缩合酯化和酸催化水解脱除异丙叉保护基两步反应合成了3个化合物,即1-(5-对硝基苯甲酰基-β-D-呋喃核糖基)-1,2,4-三氮唑-3-甲酰胺(Ⅲa),1-[5-(3,4,5-三苄氧基苯甲酰基)-β-D-呋喃核糖基]-1,2,4-三氮唑-3-甲酰胺(Ⅲb)和1-(5-苯甲酰基-β-D-呋喃核糖基)-1,2,4-三氮唑-3-甲酰胺(Ⅲc),Ⅲa和Ⅲb通过催化氢化得到1-(5-对氨基苯甲酰基-β-D-呋喃核糖基)-1,2,4-三氮唑-3-甲酰胺(Ⅳa)和1-[5-(3,4,5-三羟基苯甲酰基)-β-D-呋喃核糖基]-1,2,4-三氮唑-3-甲酰胺(Ⅳb),考察了不同碱和不同溶剂对酯化反应的影响,不同酸对脱除异丙叉保护基的影响以及催化剂Pd/C的用量对催化氢化的影响.中间体及目标产物均通过IR,1HNMR进行了结构表征.

1-[5-（4-nitrobenzoy）-β-D-ribofuranosyl]-1,2,4-triazole-3-carboxamide（IIIa）,1-[5-（3,4,5-tribenzyl-oxybenzoyl）-β-D-ribofuranosyl]-1,2,4-triazole-3-carboxamide（IIIb） and 1-（5-benzoyl-β-D-ribofuranosyl）-1,2,4-triazole-3-carboxamide（IIIc） were synthesized from 1-[2,3-O-（1-methylethylidene）-D-ribofuranosyl]-1,2,4-triazole-3-carboxamide（I） through the esterification with three different acyl chloride catalyzed by base and the hydrolysis catalyzed by p-TsOH.Then,1-[5-（4-aminobenzoyl）-β-D-ribofuranosyl]-1,2,4-triazole-3-carboxamide（IVa） and 1-[5-（3,4,5-trihydroxybenzoyl）-β-D-ribofuranosyl]-1,2,4-triazole-3-carboxamide（IVb） were obtained by means of catalytic hydrogenation.Moreover,the intermediates and title compounds were confirmed by means of IR and 1H NMR,and the effects of different kinds of bases and solvents on the esterification,different kinds of acids on the deprotection reaction and Pd/C dosage on the catalytic hydrogenation were investigated.The results show that（1） the esterification,with pyridine as the acid-binding agent and the solvent,is of high yield and good selectivity,and the conversion rate is up to more than 95%;（2） p-TsOH is a suitable catalyst for the deprotection reaction with fewer by-products;and（3） the conversion becomes complete at a mass ratio of Pd/C to compound IIIa of 0.10.