Ready Transformation of Partially Unprotected Thioglycosides into Glycosyl Fluorides Mediated by NIS/HF–Pyridine or Et₃N·3HF

Abstract

Abstract The transformation of partially unprotected phenyl 1‐thioglycosides into glycosyl fluorides can be conveniently carried out by treatment with NIS in the presence of HF–pyridine. Other sources of halonium ions such as NBS, IDCP, have also been employed. The combination NIS/Et 3 N · 3HF, where triethylamine–tris(hydrogen fluoride) (Et 3 N · 3HF) replaces HF–pyridine, can also effect this transformation when acid‐sensitive substituents are present. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)