
%0 Journal Article
%A Engelhardt, LM 
%A Mocerino, M 
%A Stick, RV 
%A White, AH 
%T A Curious By-Product in the Tipson-Cohen Reaction of a Carbohydrate Ditosylate
%J Australian Journal of Chemistry
%D 1990/06/01
%V 43
%N 6
%P 1111-1117
%K 
%R https://doi.org/10.1071/CH9901111
%U https://www.publish.csiro.au/paper/CH9901111 
%X The treatment of methyl 4,6-O-benzylidene-2,3-di-O-p-toluenesulfony-&#946;- D- galactoside , methyl 4,6-O-benzylidene-3-O-benzenesulfonyl-2-O-p- toluenesufonyl-&#946;-D-galactoside and methyl 4,6-O-benzylidene-2-O- benzenesulfonyl-3-O-p-touenesulfonyl-&#946;-D-galactoside under Tipson-Cohen conditions (Zn/ Nal/dimethylformamide ) gives mainly the alkene, methyl 4,6-O-benzylidene-2,3-dideoxy-&#946;-D-threo-hex-2-enoside. However, the first two glycosides give methyl 4,6-O-benzylidene-3-deoxy-3-C-(m-methylphenyl )-&#946;-D- galactoside, and the last, methyl 4,6-O-benzylidene- 3-deoxy-3-C-phenyl-&#946;-D-gaactoside, as minor by-products resulting from a curious reaction of the supposed iodo sulfonate intermediate. The structure of methyl 4,6-O-benzylidene-3-deoxy-3-C-(m- methylphenyl )-&#946;-D- galactoside was confirmed by a single-crystal X-ray structure determination of the derived p-bromobenzoate. 
