Abstract
O-Glycosylation is a critically important and recurring step in the synthesis of oligosaccharides
and other natural and non-natural products. While many approaches to O-glycosylation
have been reported, those strategies involving remote activation are distinguished
by the mildness and orthogonality that they often engender. As a result, O-glycosylation
using remote activation strategies has been utilized successfully in the synthesis
of complex molecules that include oligosaccharides and macrolides. Herein, we discuss
a number of contributions that have been made to this area since the 1970s. This includes
our own recent contribution involving the visible-light activation of 4-p-methoxyphenyl-3-butenylthioglycosides toward O-glycosylation in the presence of Umemoto’s
reagent.
1 Introduction
2 Fraser-Reid’s Development of n-Pentenylglycosides as Glycosyl Donors
3 Hanessian’s Remote Activation of 2-Pyridylthioglycosides
4 Gold-Catalyzed O-Glycosylation (Hotha and Yu)
5 Wan’s ‘Interrupted Pummerer’ Approach to O-Glycosylation
6 O-Glycosylation with 4-p-Methoxyphenyl-3-butenylthioglycosides
7 Conclusions
Key words
glycosylation - remote activation - oligosaccharides - visible light - photochemistry
