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Carbohydr Res. 2012 Oct 1;360:8-18. doi: 10.1016/j.carres.2012.07.012. Epub 2012 Jul 25.

Convenient syntheses of 1,2-trans selenoglycosides using isoselenuronium salts as glycosylselenenyl transfer reagents.

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1
Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen Pf 20, Hungary.

Abstract

Se-glycosyl-isoselenuronium salts such as three and four which can be prepared in one high-yielding step from acetohalogeno sugars proved to be convenient starting materials for the syntheses of a variety of selenoglycosides. Reaction with (ar)alkyl halides proceeds under mild conditions, in short time, at room temperature to afford the corresponding selenoglycosides in good yields. Aryl halides react to appreciable extent only if bearing activating nitro groups on the aromatic ring. Reactions with acylating reagents such as acetic anhydride and benzoyl chlorides furnished anomeric selenoesters some of which were recently proposed as starting compounds for alternative selenoglycoside syntheses. Selenodisaccharides with two different monosaccharide units could also be prepared via reactions of glycosyl-isoselenuronium salts with monosaccharide derivatives bearing primary or secondary triflate groups.

PMID:
22975274
DOI:
10.1016/j.carres.2012.07.012
[Indexed for MEDLINE]

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