Organic Chemistry

Visible Light Promoted Stereoselective C(sp3)-H Glycosylation for the Synthesis of C-Glycoamino Acids and C-Glycopeptides

Authors

Abstract

Glycosylative modification of peptides could improve the pharmacological properties of peptide drugs and deliver them efficiently to the target sites. Compared with O-/N-glycosides, C-glycosides exhibit more metabolic stability. We here disclose the first example of visible-light promoted and Cu-catalyzed stereoselective C-glycosylations. The mild reaction conditions are compatible with various carbohydrate substrates, including a series of mono monosaccharides and disaccharide, and is amenable to the synthesis of a wild variety of C-glycoamino acids and C-glycopeptidomimetics with good yields and excellent stereoselectivities. The dual-functional photocatalyst formed in situ via coordination of glycine derivatives and chiral phosphine Cu complex could not only catalyze the photoredox process but also control the stereoselectivity of glycosylation reaction.

Content

Thumbnail image of manu-无模板.pdf

Supplementary material

Thumbnail image of SI-final.pdf
Visible Light Promoted Stereoselective C(sp3)-H Glycosylation for the Synthesis of C-Glycoamino Acids and C-Glycopeptides
Experimental details, analytical data for all new compounds and NMR spectra.