TY - JOUR
T1 - Synthesis of 2,3-Anhydro Glycosyl Phosphonates
AU - Doan Xuan Liem, [No Value]
AU - Jenkins, I.D.
AU - Skelton, Brian
AU - White, Allan
PY - 1996
Y1 - 1996
N2 - 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.
AB - 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.
M3 - Article
SN - 0004-9425
VL - 49
SP - 371
EP - 377
JO - Australian Journal of Chemistry: an international journal for chemical science
JF - Australian Journal of Chemistry: an international journal for chemical science
ER -