Chinese Journal of Organic Chemistry >
Studies on the Total Synthesis of iso-L-Guanosine
Received date: 2019-01-27
Revised date: 2019-03-18
Online published: 2019-04-16
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
Tang Jie , Dong Xiangyou , Ouyang Wenliang , Zhu Yunlong , Ding Haixin , Xiao Qiang . Studies on the Total Synthesis of iso-L-Guanosine[J]. Chinese Journal of Organic Chemistry, 2019 , 39(9) : 2609 -2615 . DOI: 10.6023/cjoc201901045
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