
%0 Journal Article
%A Norton, AK 
%A Vonitzstein, M 
%T The Synthesis of 6-Substituted Methyl 1-O-Acetyl-3,4-anhydro-&#946;-D-Tagatofuranosides. Regioselective Chlorination and Thioacetylation in the Presence of an Oxiran
%J Australian Journal of Chemistry
%D 1996/03/01
%V 49
%N 3
%P 281-283
%K 
%R https://doi.org/10.1071/CH9960281
%U https://www.publish.csiro.au/paper/CH9960281 
%X Methyl 1-O-acetyl-6-S-acetyl-3,4-anhydro-6-thio-&#946;-D-tagatofuranoside (the 1-acetate of (2)) and methyl 1-O-acetyl-3,4-anhydro-6-chloro-6-deoxy-&#946;-D-tagatofuranoside (the 1-acetate of (3)) have been prepared as fructose derivatives by treatment of methyl 3,4-anhydro-&#946;-D-tagatofuranoside (1) with (p-dimethylaminophenyl ) diphenylphosphine/diisopropyl azodicarboxylate/thioacetic S-acid and (p- dimethylaminophenyl ) diphenylphosphine/tetrachloromethane respectively. The reactions proceed in good yield, under mild conditions, and are selective for the 6-hydroxy group. The oxiran ring is unaffected under these conditions. 
