
%0 Journal Article
%A Ferrier, RJ 
%A Furneaux, RH 
%T Photobromination of carbohydrate derivatives. VI. Functionalization at C6 of 2,3,4-Tri-O-acetyl-1,6-anhydro-&#946;-D-glucopyranose
%J Australian Journal of Chemistry
%D 1980/05/01
%V 33
%N 5
%P 1025-1036
%K 
%R https://doi.org/10.1071/CH9801025
%U https://www.publish.csiro.au/paper/CH9801025 
%X Photobromination of 2,3,4-tri-O-acetyl-1,6-anhydro-&#946;-D-glucopyranose gives the syrupy 6S (exo) bromide in high yield; further reaction leads to secondary bromination at this position. The monobromide reacts with methanol and thiophenol under conditions of kinetic control to give mainly the endo-methoxy and -phenylthio derivatives formed by direct nucleophilic displacement, and from the latter the exo-methoxy acetal was obtained by a second nucleophilic substitution. Acetolysis of these compounds can lead to the corresponding exo-6-acetoxy ester or monocyclic products formed by opening of the five-membered rings. 
