1-乙酰氧基-2,3,5-三-苯甲酰氧基-β-D-呋喃核糖的合成工艺改进  

Improved Synthesis of 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

作　　者：邓燕[1] 陶德良[1] 张永强[1] 谢维跃 

机构地区：[1]湖南工业大学湖南省绿色包装与生物纳米技术应用重点实验室,湖南株洲412008 [2]湖南轻工研究院,湖南长沙410015

出　　处：《精细化工中间体》2009年第5期30-33,共4页Fine Chemical Intermediates

基　　金：国家自然科学基金资助项目(60571032);湖南省自然科学基金资助项目(06JJ4012);湖南省科技计划资助项目(2007FJ4050)

摘　　要：以D-核糖为原料经甲基化、苯甲酰化、乙酰化合成了1-乙酰氧基-2,3,5-三-苯甲酰氧基-β-D-呋喃核糖。系统地研究了物料配比、反应时间、反应温度对产品收率的影响。较佳的制备工艺为:5.0g(0.033mol)D-核糖溶于20mL盐酸/甲醇中,于20℃下反应3h,所得产物再溶于50mL吡啶中,滴加15mL(0.129mol)苯甲酰氯,于10℃下反应15h,所得产物溶于40mL冰醋酸和5mL(0.083mol)醋酸酐中,滴加3mL浓硫酸于10℃反应15h,即得产品,总收率达74.34%(HPLC纯度98.1%)。整个路线反应条件温和、原料价廉易得,有利于工业化规模生产。用红外光谱、质谱以及核磁共振氢谱对产物进行了表征。1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose was synthesized by using D-ribose as the starting material through methylation, benzoylation and acetylization. Effects of the ratio of reactants, reaction time, and reaction temperature on the yield of the product were studied in detail. The optimal reaction conditions were obtained as follows： 5.0 g （0.033 mol） D-ribose was dissolved in 20 mL HC1/MeOH, followed by stirring the solution at 20℃ for 3 h. The reaction product was dissolved in 50 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 （0.053 mol） acetic anhydride, then 3 mL oil of vitriol was added, the solution was stirred at 10℃ for 15 h to get the final product. By means of the above process, the total yield of l-O-acetyl-2,3,5-tri-O- benzoyl-beta-D-ribofuranose was up to 74.34% （HPLC purity：98.1% ）. The feasibility for production with mild reaction conditions and cheap raw materials make it easy to produce 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D- ribofuranose in large scale. Structure of the product was identified by IR, MS and IH NMR characterization.

关 键 词：1-乙酰氧基-2 3 5-三-苯甲酰氧基-β-D-呋喃核糖 合成 D-核糖 改进 

分 类 号：Q532.4[生物学—生物化学]