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Synthesis 2010(10): 1617-1620  
DOI: 10.1055/s-0029-1218722
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Stereoselective Synthesis of 2,3-Unsaturated Thioglycopyranosides Employing Molecular Iodine

Basi V. Subba Reddy*a, Ch. Divyavania,b, Jhillu S. Yadava
a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: basireddy@iict.res.in ;
b IICT - An Associate Institution of the University of Hyderabad, Hyderabad 500007, India
Further Information

Publication History

Received 29 January 2010
Publication Date:
06 April 2010 (online)

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Abstract

Molecular iodine has been utilized for the first time for the thioglycosidation of d-glycals with various thiols to afford the corresponding 2,3-unsaturated thioglycosides in high yields. In the case of tri-O-acetyl-d-glucal, the α-anomer was obtained exclusively. The use of readily available iodine makes this method quite simple, more convenient, and practical.

Key words

glycals - iodine - thioglycosides - thia-Ferrier rearrangement

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