Streamlined Synthesis of Per-O-acetylated Sugars, Glycosyl Iodides, or Thioglycosides from Unprotected Reducing Sugars1

Mukhopadhyay, Balaram, Kartha, K. P. Ravindranathan, Russell, David A. and Field, Robert A. (2004) Streamlined Synthesis of Per-O-acetylated Sugars, Glycosyl Iodides, or Thioglycosides from Unprotected Reducing Sugars1. Journal of Organic Chemistry, 69 (22). pp. 7758-7760. ISSN 0022-3263

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Abstract

Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Related URLs:
Depositing User: Rachel Smith
Date Deposited: 21 Jan 2011 16:53
Last Modified: 24 Jul 2019 16:45
URI: https://ueaeprints.uea.ac.uk/id/eprint/19735
DOI: 10.1021/jo048890e

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