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Synthesis 2015; 47(22): 3529-3541
DOI: 10.1055/s-0034-1378829
DOI: 10.1055/s-0034-1378829
paper
Synthesis of 2,3-Unsaturated Alkynyl O-Glucosides from Tri-O-acetyl-d-glucal by Using Montmorillonite K-10/Iron(III) Chloride Hexahydrate with Subsequent Copper(I)-Catalyzed 1,3-Dipolar Cycloaddition
Further Information
Publication History
Received: 29 April 2015
Accepted after revision: 25 June 2015
Publication Date:
13 August 2015 (online)
Abstract
Two strategies were considered for the synthesis of 2,3-unsaturated O-glucosyl-1,2,3-triazoles. The first, involving reaction between tri-O-acetyl-d-glucal and triazole alcohols gave no stereoselectivity. A second strategy provided 2,3-unsaturated O-glycosides from glycals and alkynols through a Ferrier rearrangement; this method, employing montmorillonite K-10 doped with iron(III) chloride hexahydrate in dichloromethane afforded new glycosides in good to excellent yields within short times and with high α-stereoselectivities. Subsequently, the glucosides were coupled with 2-azido-1,4-naphthoquinone to produce a new series of 1,2,3-1H-triazolyl O-glucoside derivatives through a click reaction.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378829.
- Supporting Information
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