
%0 Journal Article
%A Desai, T 
%A Gigg, J 
%A Gigg, R 
%T The Allyl Group for Protection in Carbohydrate Chemistry. XXXI. Conversion of Allyl 2,6-Di-O-benzyl-&#945;-D-galactopyranoside Into Allyl 2,6-Di-O-benzyl-&#945;-D-glucopyranoside and 2,6-Di-O-benzyl-D-glucopyranose
%J Australian Journal of Chemistry
%D 1996/03/01
%V 49
%N 3
%P 305-309
%K 
%R https://doi.org/10.1071/CH9960305
%U https://www.publish.csiro.au/paper/CH9960305 
%X Allyl 2,6-di-O-benzyl-&#945;-D-galactopyranoside was converted by tin-mediated alkylation into the 3-O-p-methoxybenzyl ether which gave the 4-O-mesyl derivative. Sodium benzoate in refluxing N,N-dimethylformamide converted the last compound into allyl 4-O-benzoyl-2,6-di-O-benzyl-3-O-p-methoxybenzyl-&#945;-D-glucopyranoside in high yield. This was saponified and the product was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to give the required allyl 2,6-di-O-benzyl-&#945;-D-glucopyranoside whose structure was confirmed by conversion into the known 2,3,4,6-tetra-O-benzyl-D-glucopyranose. Removal of the allyl group from allyl 2,6-di-O-benzyl-&#945;-D-glucopyranoside by a standard procedure gave 2,6-di-O-benzyl-D-glucopyranose. Both of the title compounds are required as intermediates for the synthesis of analogues of the 'adenophostins'. 
