Glycosylation chemistry promoted by iodine monobromide: Efficient synthesis of glycosyl bromides from thioglycosides, and O-glycosides from 'disarmed' thioglycosides and glycosyl bromides

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Kartha, K. P. Ravindranathan and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (1997) Glycosylation chemistry promoted by iodine monobromide: Efficient synthesis of glycosyl bromides from thioglycosides, and O-glycosides from 'disarmed' thioglycosides and glycosyl bromides. Tetrahedron Letters, 38 (47). pp. 8233-8236. ISSN 0040-4039

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Abstract

Iodine monobromide has been found to be an efficient reagent for the conversion of both 'armed' and 'disarmed' thioglycosides (-SMe, -SPr(i), - SPh) into glycosyl bromides. This reagent is compatible with most common protecting groups, and O-glycosidic linkages. The additional potency of I- Br, compared to iodine, as an iodonium ion source also permits the glycosylation of sugar alcohols by 'disarmed' glycosyl bromides and thioglycosides.

Item Type:	Article
Uncontrolled Keywords:	biochemistry,drug discovery,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:	11 Sep 2024 09:30
Last Modified:	25 Sep 2024 18:09
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96709
DOI:	10.1016/s0040-4039(97)10124-1

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