Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2609-2615.DOI: 10.6023/cjoc201901045 Previous Articles     Next Articles

ARTICLE

L-鸟嘌呤异核苷的全合成研究

唐杰, 董祥有, 欧阳文良, 朱云龙, 丁海新, 肖强   

  1. 江西科技师范大学有机功能分子研究所 江西省有机功能分子重点实验室 南昌 330013
  • 收稿日期:2019-01-27 修回日期:2019-03-18 出版日期:2019-09-25 发布日期:2019-04-16
  • 通讯作者: 丁海新, 肖强 E-mail:xiaoqiang@tsinghua.org.cn;dinghaixin@163.com
  • 基金资助:

    国家自然科学基金(Nos.21462019,21676131)、江西省科技厅重点(No.20143ACB20012)和江西科技师范大学博士启动基金(No.2018BSQD022)资助项目.

Studies on the Total Synthesis of iso-L-Guanosine

Tang Jie, Dong Xiangyou, Ouyang Wenliang, Zhu Yunlong, Ding Haixin, Xiao Qiang   

  1. Jiangxi Key Laboratory of Organic Chemistry, Institute of Organic chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013
  • Received:2019-01-27 Revised:2019-03-18 Online:2019-09-25 Published:2019-04-16
  • Contact: 10.6023/cjoc201901045 E-mail:xiaoqiang@tsinghua.org.cn;dinghaixin@163.com
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21462019, 21676131), the Bureau of Science & Technology of Jiangxi Province (No. 20143ACB20012) and the Jiangxi Science & Technology Normal University (Doctor Startup Fund No. 2018BSQD022).

An improved route for the total synthesis of iso-L-guanosine was developed. Using L-ribose as the starting material, 3,5-O-dibenzyl-1-deoxy-L-ribose was firstly synthesized. Then, Mitsunobu reaction between N2,N2-bis(tert-butyloxycarbonyl)-6-chloro-guanine and 3,5-O-dibenzyl-1-deoxy-L-ribose afforded isonucleoside 6. Finally, iso-L-guanosine was synthesized in 9 steps with 37.3% overall yield. Adopting Mitsunobu reaction as the key step, it has the merits of high steroseletivity and regioselectivity, mild reaction condition, and high yield. Currently developed approach could be used as a general synthetic strategy for the synthesis other related guanine isonucleosides.

Key words: nucleosides, total synthesis, glycosidation, Mitsunobu reaction, isonucleosides