Selective acylation and sulfonylation of 4,6-O-benzylidene-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-glucopyranose.

Selective acylation and sulfonylation of 4,6-O-benzylidene-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-glucopyranose were systematically studied by introducing different electrophiles under the action of catalysts DMAP or Ag2O. As a result, 18 novel mono-protected compounds at the 2- or 3-position of the C-glucoside were prepared and their structures were confirmed by ¹H-NMR, 13C-NMR, 2D NOEs and HRMS analysis. The results showed that electrophiles play a significant role in determining the product distribution. [ABSTRACT FROM AUTHOR]