Sequential One-Pot Glycosidations Catalytically Promoted: Unprecedented Strategy in Oligosaccharide Synthesis for the Straightforward Assemblage of the Antitumor PI-88 Pentasaccharide

Abstract

The pentasaccharide sequence of the most active components of the antitumor drug PI-88, currently in phase II clinical trial, has been rapidly assembled in high overall yield and in only three steps starting from three monosaccharide building blocks. The procedure takes advantage of the first reported strategy of sequential one-pot glycosidations conducted exclusively under catalytic activation. In addition, the procedure relies only on shelf-stable and mild promoters such as Yb(OTf)(3) and Bi(OTf)(3).