Synthesis of 2,3-Anhydro Glycosyl Phosphonates

[No Value] Doan Xuan Liem, I.D. Jenkins, Brian Skelton, Allan White

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)371-377
JournalAustralian Journal of Chemistry: an international journal for chemical science
Volume49
Publication statusPublished - 1996

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