An Efficient Method for the Synthesis of 2,3-Unsaturated Glycopyranosides Catalyzed by Bismuth Trichloride in Ferrier Rearrangement

N. Raghavendra Swamy; Y. Venkateswarlu

doi:10.1055/s-2002-23551

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Synthesis 2002(5): 0598-0600
DOI: 10.1055/s-2002-23551

SHORTPAPER

An Efficient Method for the Synthesis of 2,3-Unsaturated Glycopyranosides Catalyzed by Bismuth Trichloride in Ferrier Rearrangement [1]

N. Raghavendra Swamy, Y. Venkateswarlu*
Organic Chemistry Division-1, Indian Institute Of Chemical Technology, Hyderabad, 500 007 India
Fax: +91(40)7160512; e-Mail: luchem@iict.ap.nic.in;

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Publication History

Received 10 November 2001
Publication Date:
02 April 2002 (online)

Abstract
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Abstract

The reaction of tri-O-acetyl-d-glucal and tri-O-benzyl-d-glucal with various alcohols and thiols to afford the corresponding glycopyranosides in excellent yields by bismuth trichloride in acetonitrile at ambient temperature has been demonstrated.

Key words

Ferrier rearrangement - carbohydrates - bismuth trichloride - unsaturated glycopyranosides

1

IICT Communication No. 01/09/07.

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1

IICT Communication No. 01/09/07.