Citation: 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 shu

Studies on the Total Synthesis of iso-L-Guanosine

Jiangxi Key Laboratory of Organic Chemistry, Institute of Organic chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013

Corresponding author: Ding Haixin, dinghaixin@163.com Xiao Qiang, xiaoqiang@tsinghua.org.cn
Received Date: 27 January 2019
Revised Date: 18 March 2019
Available Online: 16 September 2019
Fund Project: 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)the Jiangxi Science & Technology Normal University 2018BSQD022the Bureau of Science & Technology of Jiangxi Province 20143ACB20012the National Natural Science Foundation of China 21676131the National Natural Science Foundation of China 21462019

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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.
- nucleosides,
- total synthesis,
- glycosidation,
- Mitsunobu reaction,
- isonucleosides
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