Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars

Mukhopadhyay, Balaram, Kartha, K. P. Ravindranathan, Russell, David A. and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2004) Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars. 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 (former - to 2024) Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
UEA Research Groups:	Faculty of Science > Research Groups > Physical and Analytical Chemistry (former - to 2017)
Depositing User:	Rachel Smith
Date Deposited:	21 Jan 2011 16:53
Last Modified:	24 Sep 2024 10:06
URI:	https://ueaeprints.uea.ac.uk/id/eprint/19735
DOI:	10.1021/jo048890e

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