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Synlett 2010(14): 2174-2178  
DOI: 10.1055/s-0030-1258498
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Solvent-Free and Stereoselective Synthesis of C-Glycosides by Michael-Type Addition of Enamino Esters to 2-Nitro-d-glucal

Ti Zhanga,b, Chu-Yi Yu*a, Zhi-Tang Huang*a, Yue-Mei Jiaa
a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
Fax: +86(10)82616433; e-Mail: yucy@iccas.ac.cn;
b Graduate University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
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Publication History

Received 13 April 2010
Publication Date:
16 July 2010 (online)

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Abstract

Michael-type addition of enamino esters to 3,4,6-tri-O-benzyl-2-nitro-d-glucal under solvent-free conditions formed C-glycosides in excellent yields with high stereoselectivity. Reduction of the nitro group afforded the corresponding bicyclic 2-amino C-glycosides.

Key words

solvent-free - C-glycosides - Michael-type addition

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General experimental procedure: A mixture of 2-nitro-d-glucal 1 (1.0 mmol) and enamino ester 2 (1.2 mmol) was heated to the specified temperature in a silicone oil bath, as indicated in Table 1. The progress of the reaction was monitored by TLC. Upon completion, the reaction mixture was cooled to room temperature and purified by column chromatography using a mixture of ethyl acetate and petroleum ether as the eluent to furnish the target product.

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The crystal structures of 3d and 3i have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 778452 and 778453, respectively.