Palladium(0)-catalyzed synthesis of cyclic glucosides

Org Biomol Chem. 2015 Jan 7;13(1):248-51. doi: 10.1039/c4ob01975j.

Abstract

A highly regio- and stereo-selective synthesis of cyclic β-D-glucosides 3 via Pd(0)-catalyzed coupling cyclization of allenyl β-D-glucoside 1 and organic iodides in 20-38% yields is reported. After the deacetylation of 3, we obtained cyclic β-D-glucoses 4 in 90-97% yields, which may have SGLT2 inhibition activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyclization
  • Glucosides / chemical synthesis*
  • Glucosides / chemistry*
  • Palladium / chemistry*
  • Solvents / chemistry
  • Temperature

Substances

  • Glucosides
  • Solvents
  • Palladium