Iodine promoted glycosylation with glycosyl iodides: α-glycoside synthesis

van Well, Renate M., Kartha, K. P. Ravindranathan and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2005) Iodine promoted glycosylation with glycosyl iodides: α-glycoside synthesis. Journal of Carbohydrate Chemistry, 24 (4-6). pp. 463-474. ISSN 0732-8303

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Abstract

Glycosidation of fully acetylated glucopyranosyl iodide with methanol under the influence of iodine gave α-glucoside selectively. Use of less reactive acceptors led to the formation of α/β-mixtures. Glycosylations with fully benzoylated glucosyl iodide yielded β-glucosides only. In contrast, iodine-promoted glycosylation of serine and threonine with 2-azido-2-deoxy-glycosyl iodides, easily obtained in three steps, proceeded smoothly, resulting in only α-linked products in high yield in most cases.

Item Type:	Article
Additional Information:	Funding Information: This work was supported by an EU Marie Curie Intra-European Fellowship (to R. v W) and by the Weston Foundation. We thank the UK EPSRC Mass Spectrometry Service Centre, Swansea, for invaluable support.
Uncontrolled Keywords:	α-glycosylation,glycosyl iodine,glycosylated amino acids,iodine,biochemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School:	Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	10 Sep 2024 12:30
Last Modified:	25 Sep 2024 18:08
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96637
DOI:	10.1081/CAR-200067028

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