Litcius/Paper detail

Synthesis of <i>C</i>-acyl furanosides <i>via</i> the cross-coupling of glycosyl esters with carboxylic acids

Yongliang Wei, Jenny K.W. Lam, Tianning Diao

2021Chemical Science77 citationsDOIOpen Access PDF

Abstract

evolution to afford glycosyl radicals. This method embraces a large scope of furanoses, pyranoses, and carboxylic acids, and is readily applicable to the synthesis of a thymidine analogue and diplobifuranylone B, as well as the late-stage modification of (+)-sclareolide. The convenient preparation of the redox active glycosyl ester from native sugars and the compatibility with common furanoses exemplifies the potential of this method in medicinal chemistry.

Topics & Concepts

GlycosylChemistryAnomerRadicalCarboxylic acidCombinatorial chemistryStereochemistryOrganic chemistryCarbohydrate Chemistry and SynthesisCatalytic C–H Functionalization MethodsRadical Photochemical Reactions