Synthesis and structural analysis of 5-deoxy-5-((R)- and (S)-methylphosphinyl)-.ALPHA.,.BETA.-D-manno- and -L-gulopyranoses.
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概要
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Methyl 5,6-dideoxy-2,3-<I>O</I>-isopropylidene-6-nitro-α-D-<I>lyxo</I>-hex-5-enofuranoside (<B>10</B>) was prepared from D-mannose in 7 steps. Addition of methyl methylphosphinate to <B>10</B>, followed by the catalytic hydrogenation and diazotization, afforded methyl 5-deoxy-2,3-<I>O</I>-isopropylidene-5-[(methoxy)methylphosphinyl]-α-D-<I>lyxo</I>-hexofuranoside, which was then converted into 6-<I>O</I>-triphenylmethyl and 6-<I>O</I>-tetrahydropyranyl derivatives (<B>14</B>, <B>15</B>). By reduction with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by acid hydrolysis, both <B>14</B> and <B>15</B> provided the D-mannopyranoses (together with a minor proportion of L-gulopyranoses) having a methylphosphinylidene group in place of the ring oxygen. These were converted into 1,2,3,4,6-penta-<I>O</I>-acetyl derivatives, whose structures and conformations were established by spectroscopy.
- 公益社団法人 日本化学会の論文
著者
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Hanaya Tadashi
Department Of Chemistry Faculty Of Science Okayama University
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Yamamoto Hiroshi
Departmemt Of Chemical Engineering University Of Tokyo
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Hogg Alan
Department of Chemistry, University of Alberta
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Armour Margaret-Ann
Department of Chemistry, University of Alberta
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Ohmori Katsuhiko
Department of Chemistry, Faculty of Science, Okayama University
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