1333119-42-8Relevant articles and documents
AuIII-halide/phenylacetylene-catalysed glycosylations using 1-o-acetylfuranoses and pyranose 1,2-orthoesters as glycosyl donors
Mallick, Asadulla,Mallikharjunarao, Yakkala,Rajasekaran, Parasuraman,Roy, Rashmi,Vankar, Yashwant D.
, p. 579 - 588 (2016/02/18)
1-O-Acetylfuranoses and pyranose 1,2-orthoesters were activated with an AuIII 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. A new glycosylation method has been developed for 1-O-acetylfuranoses and pyranose 1,2-orthoesters, using AuIII halides and phenylacetylene as relay catalyst systems. Good anomeric selectivity was observed for 1-O-acetylfuranoses, and excellent selectivity was observed for pyranose 1,2-orthoesters. The corresponding glycosides were formed in moderate to good yields.