ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
Nphilic Glycosylation chemRxiv.pdf (1.12 MB)
0/0

Programmable Synthesis of 2-Deoxyglycosides

preprint
submitted on 15.03.2019 and posted on 18.03.2019 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

Logo branding

Exports