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Synthesis 2007(11): 1712-1716  
DOI: 10.1055/s-2007-966056
PAPER
© Georg Thieme Verlag Stuttgart · New York

Indium(III) Chloride/Water: A Versatile Catalytic System for the Synthesis of C-Furyl Glycosides and Trihydroxyalkyl Furan Derivatives

Jhillu S. Yadav*, B. V. S. Reddy, Mende Sreenivas, G. Satheesh
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadav@iict.res.in;
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Publication History

Received 12 March 2007
Publication Date:
11 May 2007 (online)

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Abstract

Hexose sugars undergo smooth coupling with 1,3-diketones and β-keto esters in the presence of 10 mol% of indium(III) chloride in water at 80 °C to furnish C-furyl glycosides in excellent yields, whereas pentose sugars produce trihydroxyalkyl-substituted furan derivatives with high selectivity. The reactions of cyclic ketones such as cyclohexane-1,3-dione or dimedone with d-glucose in acetonitrile at 80 °C gave the corresponding tetrahydrobenzofuranyl glycosides derivatives.

Key words

aldose - indium(III) reagents - 1,3-diones - (trihydroxyalkyl)furan - C-glycosidation