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J Am Chem Soc. 2019 May 22;141(20):8098-8103. doi: 10.1021/jacs.9b03982. Epub 2019 May 9.

Programmable Synthesis of 2-Deoxyglycosides.

Author information

1
Department of Chemistry , Yale University , New Haven , Connecticut 06520 , United States.
2
Department of Pharmacology , Yale School of Medicine , New Haven , Connecticut 06520 , United States.

Abstract

Control of glycoside bond stereochemistry is the central challenge in the synthesis of oligosaccharides. 2-Deoxyglycosides, which lack a C2 substituent to guide stereoselectivity, are among the most difficult classes of glycoside bond constructions. Here we present a method to synthesize 2-deoxysaccharides with specified glycoside bond stereochemistry using a nucleophilic carbohydrate residue and the synthetic equivalent of an alcohol electrophile. Because the configuration of the nucleophile can be precisely controlled, both α- and β-glycosides can be synthesized from the same starting material in nearly all cases examined. Stereoselectivities in these reactions are often greater than 50:1 and yields typically exceed 70%. This strategy is amenable to the stereocontrolled syntheses of trisaccharide diastereomers, and a tetrasaccharide. This method may be extensible to other classes of carbohydrates.

PMID:
31059254
DOI:
10.1021/jacs.9b03982

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