Stereoselective Syntheses of α-Glucuronides Using Dehydrative Glycosylation

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Abstract

Methyl and benzyl 2,3,4-tri-<i>O</i>-benzyl-<FONT SIZE="-2">D</FONT>-glucopyranuronates, prepared from <FONT SIZE="-2">D</FONT>-glucurono-6,3-lactone, afforded selectively the corresponding <i>α</i>-glucopyranosiduronates by the aid of the condensing reagent system composed of <i>p</i>-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine. Using this method, <i>O</i>-<i>α</i>-<FONT SIZE="-2">D</FONT>-glucopyranuronosyl-(1→3)-<i>O</i>-<i>α</i>-<FONT SIZE="-2">L</FONT>-arabinofuranosyl-(1→3)-<FONT SIZE="-2">D</FONT>-xylopyranose, one of the minimal component units in the structure of plantago-mucilage A from the seeds of <i>Plantago asiatica</i> Linné constituting a Chinese medicine : chegianzi [<SUB></SUB>].

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 69(11), 3247-3259, 1996-11-15

    The Chemical Society of Japan

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  • Systematic Synthesis and Molecular analysis of the Biologically Functional Glycoconjugates, and Application as Indispensable Probes for the Life Sciences  [in Japanese]

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Codes

  • NII Article ID (NAID)
    10008911055
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    Journal Article
  • ISSN
    00092673
  • NDL Article ID
    4098863
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  CJPref  NDL  J-STAGE 
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