Palladium‐Catalysed C(sp<sup>3</sup>)−H Glycosylation for the Synthesis of C‐Alkyl Glycoamino Acids
Yichu Liu, Yibing Wang, Wenhao Dai, Wei Huang, Yingxia Li, Hong Liu
Abstract
Abstract We have developed a highly efficient and practical approach for palladium‐catalyzed trifluoroacetate‐promoted N‐quinolylcarboxamide‐directed glycosylation of inert β‐C(sp 3 )−H bonds of N‐phthaloyl α‐amino acids with glycals under mild conditions. For the first time, C(sp 3 )−H activation for glycosylation was achieved to build C‐alkyl glycosides. This method facilitates the synthesis of various β‐substituted C‐alkyl glycoamino acids and offers a tool for glycopeptide synthesis.
Topics & Concepts
GlycosylationPalladiumChemistryAlkylGlycopeptideCatalysisAmino acidCombinatorial chemistryStereochemistryOrganic chemistryBiochemistryAntibioticsCarbohydrate Chemistry and SynthesisChemical Synthesis and AnalysisPeptidase Inhibition and Analysis