以鸟苷为原料合成2-异肌苷  

Synthesis of 2-isoinosine from guanosine

作　　者：马冠军 李甲 卢田田 张伟[1] 孙莉萍[1] 陈磊山[1] 夏然[3] MA Guan-jun;LI Jia;LU Tian-tian;ZHANG Wei;SUN Li-ping;CHEN Lei-shan;XIA Ran(School of Life Sciences&Basic Medicine,Xinxiang University,Xinxiang 453003,China;Xinxiang Tuoxin Pharmaceutical Co.,Ltd,Xinxiang 453000,China;School of pharmacy,Xinxiang University,Xinxiang 453003,China)

机构地区：[1]新乡学院,生命科学与基础医学学院,河南新乡453003 [2]新乡拓新药业股份有限公司,河南新乡453000 [3]新乡学院,药学院,河南新乡453003

出　　处：《化学研究与应用》2021年第2期381-386,共6页Chemical Research and Application

基　　金：国家自然科学基金项目(21602189)资助;2019年河南省大学生创新创业训练计划项目(S201911071007)资助。

摘　　要：以廉价的鸟苷为原料,经过乙酰基保护糖环上的羟基,再和POCl 3反应,将6-位羰基转化为氯原子,继而还原脱除氯原子,然后在亚硝酸异戊酯作用下发生重氮化反应,将2-位氨基转化为羟基,最后脱除乙酰基,以5步和56%的总收率得到2-异肌苷。重氮化优化的反应条件是:6倍量的亚硝酸异戊酯为重氮化试剂、CHCl 3/H 2O为混合溶剂,60℃反应6 h,收率86%。关键反应步骤中,脱氯和重氮化反应规模可以分别扩大到200 g和100 g。该方法原料廉价易得,产物成本低,解决了传统方法中原料价格高的问题,具有一定的应用前景。2-Isoinosine was synthesized from commercially available guanosine in 5 steps and 56%total yield.6-Cl was formed from carbonyl group of guanosine via acetylation and chlorination,and then was removed by catalytic reduction.2-NH 2 was transformed into carbonyl group by diazotization reaction with isoamyl nitrite.The optimal reaction condition of diazotization involved in 6 equivalents of isoamyl nitrite using CHCl 3/H 2O as mixed solvent at 60℃for 6 hours and the yield was 86%.The dechlorination and diazotization steps could be scaled up to 200 g and 100 g scales respectively.This method took advantages of accessible starting reactants and lower product cost,which dissolved the problems in the traditional methods,making this method more attractive for application.

关 键 词：鸟苷 2-异肌苷 氯代 重氮化反应 

分 类 号：O626.32[理学—有机化学]