Chinese Journal of Organic Chemistry >
Studies on the Total Synthesis of iso-L-Cystidine
Received date: 2016-05-19
Revised date: 2016-07-04
Online published: 2016-07-15
Supported by
Project supported by National Natural Science Foundation of China (No.21462019),the New Century Excellent Talents in University (No.11-1000),and the Bureau of Science&Technology of Jiangxi Province (No.20143ACB20012).
In order to systematic study the biological effects of isonucleoside incorporated oligonucleotides, an efficient synthetic process for iso-L-cystidine was investigated in present paper. Using L-ribose as starting material, iso-L-cystidine was obtained in 9 steps and 28.5% overall yield. The key step was the regioselective nucleophilic substitution of 5-O-triphenylmethane-2,3-O-cyclic sulfate with uracil. After extensive optimization, it was found that using cesium carbonate as base can improve significantly the N-1 glycosidic bond formation and reduce the side reactions. At the same time, a N-1,N-3 doublic 1-deoxyribose substituted iso-L-uridine was identified for the first time. The present reported synthetic process has the merits of mild reaction conditions, easy purified intermediates and high overall yield, which could be used as a general synthetic approach for the preparation other related isonucleoside.
Sun Zhidong , Zhu Yunlong , Huang Haiyang , Song Xianrong , Xiao Qiang . Studies on the Total Synthesis of iso-L-Cystidine[J]. Chinese Journal of Organic Chemistry, 2016 , 36(11) : 2729 -2734 . DOI: 10.6023/cjoc201605036
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