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Synthesis 2008(13): 1994-1996  
DOI: 10.1055/s-2008-1067121
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

A Novel and Convenient Synthesis of Thiazol-2(3H)-imine-Linked Glyco­conjugates

Guo-Bin Zhou*a, Yue-Qing Guana, Chao Shenb, Qian Wanga, Xiao-Ming Liua, Peng-Fei Zhang*b, Li-Li Lia
a College of Chemical and Environmental Engineering, Shandong University of Science and Technology, Qingdao, Shandong 266510, P. R. of China
Fax: +86(532)86057718; e-Mail: gbzhou_zju@sdust.edu.cn;
b College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, P. R. of China
Fax: +86(571)88484468; e-Mail: pfzhang@hznu.edu.cn;
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Publication History

Received 4 March 2008
Publication Date:
11 June 2008 (online)

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Abstract

A novel and convenient synthetic approach for the preparation of thiazol-2(3H)-imine-linked glycoconjugates, which involves the cyclization of 1-benzoyl-3-(2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranosyl)thiourea with a variety of carbonyl compounds bearing an α-H in the presence of [hydroxy(tosyloxy)iodo]benzene (HTIB) and triethylamine, has been developed. The methodology has advantages such as avoiding the use of lachrymatory and toxic bromine, simplicity of procedure, mild reaction conditions, and high yields.

Key words

thiazol-2(3H)-imine - glycoconjugate - [hydroxy(tosyl­oxy)iodo]benzene - synthesis