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Synthesis 2011(9): 1442-1446  
DOI: 10.1055/s-0030-1259975
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient and Practical Synthesis of 5′-Deoxytubercidin and Its Analogues via Vorbrüggen Glycosylation

Yang Songa, Haixin Dingb, Yanhui Doub, Ruchun Yangb, 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 January 2011
Publication Date:
30 March 2011 (online)

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Abstract

An efficient and practical synthesis of naturally occurring marine nucleosides 5′-deoxytubercidins on a 10 gram scale in good overall yield is reported. The key step was the Vorbrüggen glycosylation of pyrrolo[2,3-d]pyrimidines with 5-deoxy-1,2,3-tri-O-acetyl-β-d-ribofuranose.

Key words

5′-deoxytubercidin - Vorbrüggen glycosylation - pyrrolo[2,3-d]pyrimidine - marine nucleoside - 7-deazapurine