A convenient synthesis of 1,2,4-tri-O-acetyl-5-deoxy-5-((R)-and (S)-ethylphosphino and phenylphosphino)-3-O-methyl-.ALPHA.,.BETA.-D-xylopyranoses and their phosphinothioyl derivatives.
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概要
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1,2,4-Tri-<I>O</I>-acetyl-5-deoxy-5-[(<I>R</I>)- and (<I>S</I>)-ethylphosphinyl]-3-<I>O</I>-methyl-α,β-D-xylopyranoses (<B>8a–d</B>) were prepared from 5-deoxy-5-[(<I>R</I>)- and (<I>S</I>)-(ethoxy)ethylphosphinyl]-1,2-<I>O</I>-isopropylidene-3-<I>O</I>-methyl-α-D-xylofuranoses in two steps. Reduction of <B>8a–d</B> and their 5-(phenylphosphinyl) congeners with trichlorosilane- triethylamine in benzene smoothly afforded the corresponding title 5-deoxy-5-phosphino-D-xylopyranoses (<B>9a–d</B> and <B>14a–d</B>) without causing inversion of the ring-phosphorus atom. Treatment of <B>9a–d</B> and <B>14a–d</B> with sulfur in benzene efficiently provided the corresponding (phosphinothioyl)-in-ring D-xylopyranoses. Structural and conformational assignments of these newly obtained compounds were made on the basis of mass and NMR (<SUP>1</SUP>H and <SUP>31</SUP>P) spectral data.
- 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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Shigetoh Nobuyuki
Department of Chemistry, Faculty of Science, Okayama University
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