Contrasting reactivity of thioglucoside and selenoglucoside donors towards promoters: Implications for glycosylation stereocontrol

van Well, Renate M., Kärkkäinen, Tiina S., Kartha, K. P. Ravindranathan and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2006) Contrasting reactivity of thioglucoside and selenoglucoside donors towards promoters: Implications for glycosylation stereocontrol. Carbohydrate Research, 341 (10). pp. 1391-1397. ISSN 0008-6215

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Abstract

The stereochemical outcome of glycosylation reactions with model thioglycosides and selenoglycosides proved to be dependent on the source of promoter iodonium ion, with iodine giving different results to N-iodosuccinimide (NIS) alone or N-iodosuccinimide/trimethylsilyltrifluoromethanesulfonate (NIS/TMSOTf). In contrast to armed thioglycosides, which anomerise, and disarmed thioglycosides, which do not react, both armed and disarmed selenoglycosides give rise to the corresponding glycosyl iodides when reacted with iodine. Further, whilst the single electron transfer agent DDQ alone is an ineffective promoter, in combination with iodine it produces better acetonitrile-assisted β-stereoselectivity with both thioglycosides and selenoglycosides than does tris(4-bromophenyl)aminium hexachloroantimonate (BAHA).

Item Type:	Article
Additional Information:	Funding Information: We thank the EU (Marie Curie Intra-European fellowship to R. M. van W.), the AICR (studentship to T.S.K.) and The Weston Foundation for funding. We are indebted to the EPSRC Mass Spectrometry Service Centre, Swansea, for invaluable support.
Uncontrolled Keywords:	glycosylation,mechanism,promoter,selenoglycoside,thioglycoside,analytical chemistry,biochemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1602
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/96633
DOI:	10.1016/j.carres.2006.04.029

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