文献类型：期刊文献

中文题名：腺嘌呤葡萄糖苷的合成

英文题名：SYNTHESIS OF 9-(β-D-GLUCOPYRANOSYL)ADENINE

作者：孙莉萍[1];孙明明[2];夏然[2];渠桂荣[3]

第一作者：孙莉萍

机构：[1]新乡学院生命科学技术学院;[2]新乡学院化学化工学院;[3]河南师范大学化学化工学院

第一机构：新乡学院生命科学技术学院

年份：2018

卷号：35

期号：4

起止页码：41-45

中文期刊名：精细石油化工

外文期刊名：Speciality Petrochemicals

收录：CSTPCD;;Scopus;北大核心:【北大核心2017】；CSCD:【CSCD2017_2018】；

基金：国家自然科学基金(21602189);河南省科技发展计划项目(172102310212和172102310213);河南省高等学校重点科研项目(16A150042和16A180035);新乡学院科技创新团队项目(XXUTD20170106)资助

语种：中文

中文关键词：腺嘌呤葡萄糖苷;β-D-(+)-五乙酰基葡萄糖;糖苷化;核苷合成

外文关键词：9-（β-D-glucopyranosyl）adenine;penta-O-acetyl-β-D-glucopyranose;glycosylating;nucleoside synthesis

摘要：以β-D-(+)-五乙酰基葡萄糖和HCl气体反应,得到1-氯-2,3,4,6-四-O-乙酰基葡萄糖,继而和硅醚化的6-氯嘌呤反应得到缩合物,缩合物在Na_2CO_3催化下脱除乙酰基,不经分离"一锅法"在饱和的NH_3/MeOH溶液中反应使6位氨解,最终以4步和80%的总收率得到腺嘌呤葡萄糖苷。考察了关键步骤缩合反应中催化剂、溶剂、投料比、反应时间、反应温度及反应规模对缩合物收率的影响,得到了较佳的反应条件:乙腈为溶剂,2%四氯化锡为催化剂,n(6-氯嘌呤)∶n[β-D-(+)-五乙酰基葡萄糖]=1∶1,60℃反应30 min,收率87%,不需要柱层析。缩合反应的反应规模可以扩大到200g,收率75%。
A new new method for the synthesis of 9-（β-D-glucopyranosyl）adenine was developed.The starting material penta-O-acetyl-β-D-glucopyranose reacted with HCl gas in the presence of acetic chloride to afford 1-chloro-tetra-O-acetyl-β-D-glucopyranose,which was glycosylated with sily-protected 6-chloropurine.The acetyl groups of glycosylated intermediate were removed by catalytic Na2CO3 in MeOH,and then the saturated NH3/MeOH solution was added in order to ammonolysis of C6 chloride.The 9-（β-D-glucopyranosyl）adenine was synthesized in 4 steps and 80%total yield.The effects of catalysts,solvents,substrate ratio,reaction time,reaction temperature and reaction scale for glycosylated intermediate were investigated,and the optimized reaction conditions were obtained：CH3CN as solvent,2% SnCl4 as catalyst,n（6-chloropurine）∶n[penta-O-acetyl-β-D-glucopyranose]=1∶1,60 ℃ for 30 min,87% yield,and the chromatography was avoided.The glycosylated step could enlarge to 200 grams in 75% yield.