Acyl and Benzyl-C-β-D-Glucosides: Synthesis and Biostudies for Glucose-Uptake-Promoting Activity in C2C12 Mytotubes

Article abstract of DOI:10.1002/ejoc.201901037

A convenient and scalable synthetic approach has been developed for the synthesis of acyl-C-β-d-glucosides and benzyl-C-β-d-glucosides. The use of Weinreb-amide (WA) functionality was crucial for this accomplishment as the other apparently capable alternatives, had severe limitations for the access to acyl-C-glucosides. The synthesized compounds, acyl and benzyl-C-glucosides promote glucose-uptake activity in the C2C12 (mouse skeletal muscle) cell lines through PPAR-γ mediated GLUT4 expression. The developed synthetic scheme for acyl-and benzyl-C-β-d-glucosides and biostudies evaluating their activity as glucose-uptake promoters are disclosed herein.