Studies on the Total Synthesis of iso-L-Cystidine

doi:10.6023/cjoc201605036

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (11): 2729-2734.DOI: 10.6023/cjoc201605036 Previous Articles Next Articles

Notes

L-胞嘧啶异核苷的全合成研究

孙志东, 朱云龙, 黄海洋, 宋贤荣, 肖强

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:2016-05-19 修回日期:2016-07-04 发布日期:2016-07-15
通讯作者: 肖强 E-mail:xiaoqiang@tsinghua.org.cn
基金资助:
国家自然科学基金（No.21462019）、教育部新世纪优秀人才支持计划（No.11-1000）、江西省科技厅重点（No.20143ACB20012）资助项目.

Studies on the Total Synthesis of iso-L-Cystidine

Sun Zhidong, Zhu Yunlong, Huang Haiyang, Song Xianrong, Xiao Qiang

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

Received:2016-05-19 Revised:2016-07-04 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).

1. Studies on the Total Synthesis of iso-L-Cystidine.PDF(894KB)

Abstract

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.

Key words: nucleosides, total synthesis, glycosidation, nucleophilic substitution, isonucleosides

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Sun Zhidong, Zhu Yunlong, Huang Haiyang, Song Xianrong, Xiao Qiang. Studies on the Total Synthesis of iso-L-Cystidine[J]. Chin. J. Org. Chem., 2016, 36(11): 2729-2734.

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L-胞嘧啶异核苷的全合成研究

Studies on the Total Synthesis of iso-L-Cystidine

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