HClO4.SiO2 catalysed synthesis of alkyl 3-deoxy-hex-2-enopyranosides from 2-hydroxy glucal ester: application in the synthesis of a cis-fused bicyclic ether and a 4-amino-C-glucoside

Gupta, Preeti ; Kumari, Nitee ; Agarwal, Aditi ; Vankar, Yashwant D. (2008) HClO4.SiO2 catalysed synthesis of alkyl 3-deoxy-hex-2-enopyranosides from 2-hydroxy glucal ester: application in the synthesis of a cis-fused bicyclic ether and a 4-amino-C-glucoside Organic and Biomolecular Chemistry, 6 (21). pp. 3948-3956. ISSN 1477-0520

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/2008...

Related URL: http://dx.doi.org/10.1039/B810654A

Abstract

A variety of alcohols react with 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabino-hex-1-enopyranose 1 in the presence of a catalytic amount of HClO4 supported on silica gel to give the corresponding alkyl 3-deoxy-hex-2-enopyranosides 2 in high yield, with short reaction times (10-45 mins) and good a-selectivity. Work-up merely involves filtration of the reagent, followed by chromatographic purification of the crude product. This methodology has also been employed in the synthesis of a bicyclic ether, a useful precursor for cyclic polyethers, and a 4-amino-C-glucoside.

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