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Synthesis 2007(19): 2967-2972  
DOI: 10.1055/s-2007-983881
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Carbohydrate-Conjugated dT Analogues Using ‘Click Chemistry’

Xuanye Jina, Ruchun Yangb, Peiyuan Jina, 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)3826894 ; e-Mail: qxiao75@yahoo.com.cn;
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Publication History

Received 15 May 2007
Publication Date:
11 September 2007 (online)

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Abstract

A new type furo[2,3-d]pyrimidine nucleoside conjugated with various carbohydrates was synthesized using Sonogashira coupling and ‘click chemistry’. In the subsequent deprotection of the 4-toluoyl and acetyl groups with catalytic sodium methoxide in methanol, the furo[2,3-d]pyrimidine rearranged to an opened ketone-type structure. Their structures were confirmed on the basis of spectroscopy.

Key words

dT analogues - carbohydrate conjugation - Sonogashira reaction - click chemistry