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%)。
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 cone. 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.
出处
《精细化工》
EI
CAS
CSCD
北大核心
2007年第10期1004-1007,1036,共5页
Fine Chemicals
基金
国家自然科学基金(60571001
20505020)
湖南省自然科学基金(06JJ4012)~~