
TY  - JOUR
A1  - Doanxuanlie, m 
A1  - Jenkins, ID 
A1  - Skelton, BW 
A1  - White, AH 
T1  - Synthesis of 2,3-Anhydro Glycosyl Phosphonates
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1996
VL  - 49
IS  - 3
SP  - 371
EP  - 377
KW  - 
UR  - https://doi.org/10.1071/CH9960371 
N2  - 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. 
ER  -

