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Synthesis 2006(8): 1301-1306  
DOI: 10.1055/s-2006-926394
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Mono- and Di-O-β-d-glucopyranoside Conjugates of (E)-Resveratrol

Zhaojun Zhang*a,b, Biao Yua, Richard R. Schmidtb
a State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
e-Mail: zhangzj99@yahoo.com.cn;
b Fachbereich Chemie, Universität Konstanz, Universitätsstrasse 10, 78457 Konstanz, Germany
Fax: +49(7531)883135;
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Publication History

Received 20 September 2005
Publication Date:
27 March 2006 (online)

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Abstract

Starting from the commercially available natural product (E)-resveratrol (1), the four selectively tert-butyldimethylsilyl (TBS) protected (E)-resveratrols 6-9 were prepared by one reaction. Using 6-9 as glucosyl acceptors and trifluoroacetimidate 11 as glucosyl donor, three bioactive natural glucopyranoside conjugates of (E)-resveratrol 2-4 and one novel compound (5) were efficiently prepared in two steps.

Key words

carbohydrates - natural products - glycosides - glyco­sylation - phenols

1

Present address: Shanghai Medicilon Inc., 67 Libing Road, Building 5, Zhangjiang High-Tech Park, Shanghai 201203, P. R. of China.