Au^III‐Halide/Phenylacetylene‐Catalysed Glycosylations Using 1‐<i>O</i>‐Acetylfuranoses and Pyranose 1,2‐Orthoesters as Glycosyl Donors

Abstract

Abstract 1‐ O ‐Acetylfuranoses and pyranose 1,2‐orthoesters were activated with an Au III halide/phenylacetylene relay catalyst system, and they acted as excellent glycosyl donors. Thus, 1‐ O ‐acetyl‐ D ‐ribofuranose, 1‐ O ‐acetyl‐ D ‐lyxofuranose, and 1,2‐orthoesters selectively gave the corresponding 1,2‐ trans glycosides, whereas 1‐ O ‐acetyl‐ D ‐arabinofuranose and 1‐ O ‐acetyl‐ D ‐xylofuranose both gave mixtures of 1,2‐ trans and 1,2‐ cis glycosides, with the 1,2‐ trans glycosides predominating.