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Synthesis 2011(8): 1213-1218  
DOI: 10.1055/s-0030-1259961
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Approach for the Synthesis of 1′-O-α-Methyl Pyrrolo[2,3-d]pyrimidine Isonucleosides

Yang Songa, Ruchun Yangb, Haixin Dingb, Qi Sunb, Qiang Xiao*b, Yong Ju*a
a Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
Fax: +86(10)62781695; e-Mail: juyong@tsinghua.edu.cn;
b Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China
Fax: +86(791)6422903; e-Mail: xiaoqiang@tsinghua.org.cn;
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Publication History

Received 26 December 2010
Publication Date:
16 March 2011 (online)

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Abstract

A series of novel 1′-O-α-methyl isonucleosides were efficiently and stereoselectively synthesized with 1,2,3,5-tetra-O-acetyl-d-ribofuranose as the starting material. The key steps include regioselective and stereoselective deprotection of the 2,4-dichlorobenzyl group at C2, triflation, and substitution with appropriate nucleobases using cesium carbonate as the base. Removal of the residual 2,4-dichlorobenzyl groups and subsequent transformation afforded the title compounds in 30-37% overall yield. The products represent a new type of isonucleosides with 1′-O-substitution.

Key words

pyrrolo[2,3-d]pyrimidine - isonucleoside - regioselective deprotection - triflate - cesium carbonate