The synthesis of dimethyl 6-O-acetyl-2,3-anhydro-alpha-D-mannopyranosylphosphonates and the corresponding alpha- and beta-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 H-1 and C-13 n.m.r. spectroscopy, and confirmed by X-ray structural analysis in the case of dimethyl 6-O-acetyl-2,3-anhydro-alpha-D-mannopyranosylphosphonate and of dimethyl 6-O-acetyl-2,3-anhydro-beta-D-allopyranosylphosphonate.
|Journal||Australian Journal of Chemistry: an international journal for chemical science|
|Publication status||Published - 1996|