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Paper | Regular issue | Vol 36, No. 11, 1993, pp.2557-2564
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6483
Synthesis of 5-Deoxy-5-hydroxyphosphinyl-D-mannopyranoses

Tadashi Hanaya, Kunihiro Hirose, and Hiroshi Yamamoto*

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


The title sugar analogues (13) were synthesized by starting with known methyl (E)-5,6-dideoxy-2,3-isopropylidiene-6-nitro-α-D-lyxo-hex-5-enofuranoside (5a) in six steps through the key intermediate, methyl 5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside(8a). The products (13) were converted into the corresponding penta-O-acetyl-5-methoxyphosphinyl derivatives (14), whose structures and conformations (mostly 4C1) were established by spectroscopy.