【摘要】 以肌苷为起始原料,经苯甲酰化、乙酰化合成了1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖。研究了物料配比、反应时间、反应温度对产品收率的影响。结果表明:适当降低反应温度、减少吡啶用量有利于提高产率。较佳的制备工艺为:9.0 g(0.034 mol)肌苷溶于40 mL吡啶中,滴加15 mL(0.129 mol)苯甲酰氯于10℃反应15 h;所得产物溶于40 mL冰醋酸和5 mL(0.083 mol)醋酸酐中,滴加3 mL浓硫酸于10℃反应17 h,即得产品,总产率达74.93%(经HPLC测定其质量分数98.0%,以下同)。并用IR、1HNMR和MS对产品进行了表征。对较佳工艺分别放大12倍和200倍进行生产验证,产品的总产率分别为74.67%(质量分数:97.9%)、74.49%(质量分数:98.0%)。更多还原

【Abstract】 To synthesize 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose(Ⅰ),9.0 g(0.034 mol) inosine was dissolved in 40 mL pyridine,then 15 mL(0.129 mol) benzoyl chloride was added,followed by stirring the solution at 10 ℃ for 15 h.The product was dissolved in a mixture of 40 mL glacial acetic acid and 5 mL(0.083 mol) acetic anhydride,then 3 mL conc.H2SO4 was added,and the solution was stirred at 10 ℃ for 17 h.By means of above optimized process,the total yield of Ⅰ was summed up to 74.93%(purity:98.0%,HPLC,mass percent).The structure of the product was identified by IR,1HNMR and MS.The synthesis process was validated by magnifying 12 times and 200 times under optimized conditions,and the total yield was summed up to 74.67%(purity 97.9%) and 74.49%(purity 98.0%),respectively.更多还原