Synthesis of 2-Deoxyglycosides Bearing Free Hydroxyl Substituents on the Glycosyl Donor.

ABSTRACT: Recent efforts in the field of carbohydrate chemistry have focused on the site- and stereocontrolled synthesis of O-glycosides derived from acceptors bearing multiple hydroxyl substituents. By comparison, there are few examples of the site-selective synthesis of O-glycosides bearing free hydroxyl substituents on the donor reagent. Here, we report the application of an umpolung glycosylation strategy to the synthesis of O-glycosides derived from donors bearing free hydroxyl substituents. The reaction proceeds via prior deprotonation of one or more free hydroxyl groups on a thiophenylglycoside donor, reductive lithiation to generate an anomeric anion intermediate, and addition of this anion to an alkyl 2-(2-methyltetrahydropyranyl) peroxide. By this approach, α-linked gl

SUBMITTER: Hoang KM 

PROVIDER: S-EPMC9511991 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature