
TY  - JOUR
A1  - Ferrier, RJ 
A1  - Furneaux, RH 
T1  - Photobromination of carbohydrate derivatives. VI. Functionalization at C6 of 2,3,4-Tri-O-acetyl-1,6-anhydro-&#946;-D-glucopyranose
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1980
VL  - 33
IS  - 5
SP  - 1025
EP  - 1036
KW  - 
UR  - https://doi.org/10.1071/CH9801025 
N2  - 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. 
ER  -

