Synthesis and structural analysis of 5-deoxy-3-O-methyl-5-C-[(R)- and (S)-phenylphosphinothioyl]-.ALPHA.- and .BETA.-D-xylopyranoses.

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概要

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• Treatment of 5-deoxy-5-iodo-1,2-<I>O</I>-isopropylidene-3-<I>O</I>-methyl-α-D-xylofuranose with ethyl phenylphosphinothioate in the presence of NaH in DMF gave a 1:1 mixture of the 5-deoxy-5-<I>C</I>-[(<I>R</I>)- and (<I>S</I>)-(ethoxy)phenylphosphinothioyl] derivatives. Reduction of these D-xylofuranoses with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the acid hydrolysis, provided the title compounds, which are the first sugar analogues having a phosphinothioyl group in the hemiacetal ring. These compounds were converted into four, separable 1,2,4-tri-<I>O</I>-acetates, the structures and conformations of which were established by spectroscopy. The corresponding per-<I>O</I>-acetyl-5-deoxy-5-<I>C</I>-[(<I>R</I>)- and (<I>S</I>)-phenylphosphinyl] analogues were also prepared and their previously presented structures were revised. Complete <SUP>1</SUP>H NMR (500-MHz) parameters of these two types of compounds are given for a comparative, structural study.

• 公益社団法人 日本化学会の論文

著者

• Shigetoh Nobuyuki

  Department of Chemistry, Faculty of Science, Okayama University

関連論文

• 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.
• Synthesis and structural analysis of 5-deoxy-3-O-methyl-5-C-[(R)- and (S)-phenylphosphinothioyl]-.ALPHA.- and .BETA.-D-xylopyranoses.

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