
%0 Journal Article
%A Doanxuanlie, m 
%A Jenkins, ID 
%A Skelton, BW 
%A White, AH 
%T Synthesis of 2,3-Anhydro Glycosyl Phosphonates
%J Australian Journal of Chemistry
%D 1996/03/01
%V 49
%N 3
%P 371-377
%K 
%R https://doi.org/10.1071/CH9960371
%U https://www.publish.csiro.au/paper/CH9960371 
%X The synthesis of dimethyl 6-O-acetyl-2,3-anhydro-&#945;-D- mannopyranosylphosphonates and the corresponding &#945;- and &#946;- allo derivatives is described. Dimethyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosylphosphonates, although unreactive towards normal epoxidizing agents (3-chloroperoxybenzoic acid, trifluoroperoxyacetic acid, etc), underwent smooth epoxidation with hydrogen peroxide in the presence of sodium tungstate or dodecatungstophosphoric acid. An interesting regiospecific  deacetylation of the 4-acetate occurred under these conditions. The structures of these anhydro  glycosyl  phosphonates were determined by 1H and 13C n.m.r. spectroscopy, and confirmed by X ray structural analysis in the case of dimethyl 6-O-acetyl-2,3-anhydro-&#945;-D-mannopyranosylphosphonate , and of dimethyl 6-O-acetyl-2,3-anhydro-&#946;-D-allopyranosylphosphonate. 
