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Nphilic Glycosylation chemRxiv.pdf (1.12 MB)

Programmable Synthesis of 2-Deoxyglycosides

preprint
submitted on 15.03.2019, 21:34 and posted on 18.03.2019, 15:15 by Seth Herzon, Kevin M. Hoang, Nicholas Lees
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. Our method offers a fundamentally new approach to O-glycoside synthesis to enable downstream biochemical and natural product applications.

History

Email Address of Submitting Author

seth.herzon@yale.edu

Institution

Yale University

Country

United States

ORCID For Submitting Author

0000-0001-5940-9853

Declaration of Conflict of Interest

None

Exports

ChemRxiv

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