Recent advances in reagent-controlled stereoselective/stereospecific glycosylation

Carbohydr Res. 2019 Feb 1:473:72-81. doi: 10.1016/j.carres.2018.10.006. Epub 2018 Oct 22.

Abstract

The formation of O-glycosidic linkage is arguably one of the most important topics in glycoscience due to the prevalence of O-glycosides in nature. Great efforts have been devoted to this field by many carbohydrate chemists to develop stereoselective/stereospecific glycosylation methodologies. Although glycosyl donor- and acceptor-controlled strategies have significantly progressed, the tedious design and pre-synthesis of substrates could not be avoided. On the other hand, reagent-controlled glycosylation can overcome these challenges and produce the desired selectivity by only altering external factors such as concentration, reagents or other reaction conditions. This mini-review discusses selected recent novel methodologies on reagent-mediated stereo-controlled glycosylation in the last decade, classified by the types of glycosyl donors.

Keywords: Glycosylation; Reagent-control; Stereoselectivity; Stereospecificity.

Publication types

  • Review

MeSH terms

  • Glycosides / chemistry*
  • Glycosylation
  • Indicators and Reagents / chemistry
  • Stereoisomerism

Substances

  • Glycosides
  • Indicators and Reagents