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Paper | Regular issue | Vol 55, No. 7, 2001, pp.1301-1309
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9235
Synthesis of 5-Deoxy-5-phosphinyl-D-galactopyranose Derivatives: New Phospha-Sugar Analogs of D-Galactose

Tadashi Hanaya,* Ken-ichi Sugiyama, Yasushi Fujii, Akihito Akamatsu, and Hiroshi Yamamoto*

*Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan


The addition reaction of dimethyl phosphonate to 3,6-di-O-benzyl-1,2-O-isopropylidene-α-L-arabino-hexofuranos-5-ulose (11), followed by deoxygenation of 5-hydroxyl group, provided 5-deoxy-5-dimethoxyphosphinyl-D-galactofuranose derivative (13a). Reduction of 13a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-galactopyranose analog (15) having a phosphinyl group in the hemiacetal ring. This was converted into the 1,2,4-tri-O-acetyl-5-methoxyphosphinyl derivatives (16), whose structure and conformation were established by 1H-NMR spectroscopy.