A Practical Large-Scale Access to 1,6-Anhydro-β-d-hexopyranoses by a Solid-Supported Solvent-Free Microwave-Assisted Procedure

Vincent Bailliez; Renata M. de Figueiredo; Alain Olesker; Jeannine Cleophax

doi:10.1055/s-2003-39168

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Synthesis 2003(7): 1015-1017
DOI: 10.1055/s-2003-39168

SHORTPAPER

A Practical Large-Scale Access to 1,6-Anhydro-β-d-hexopyranoses by a Solid-Supported Solvent-Free Microwave-Assisted Procedure

Vincent Bailliez, Renata M. de Figueiredo, Alain Olesker, Jeannine Cleophax*
Institut de Chimie des Substances Naturelles du C.N.R.S, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France
Fax: +33(1)69077247; e-Mail: Jeannine.Cleophax@icsn.cnrs-gif.fr;

Further Information

Publication History

Received 28 January 2003
Publication Date:
09 May 2003 (online)

Abstract
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Abstract

Microwave irradiation of 6-O-tosyl or 2,6-di-O-tosyl peracetylated hexopyranoses absorbed on basic alumina in a dry medium afforded the corresponding 1,6-anhydro-β-d-hexopyranoses. A direct access to 1,6:3,4-dianhydro-β-d-altropyranose (16) from d-glucose is also described.

Key words

anhydrosugars - solid support synthesis - solvent-free reactions - microwave activation - ring closure

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