分子内アグリコン転移反応と立体選択的糖鎖合成への応用  [in Japanese] Intramolecular Aglycon Delivery and Its Application to Stereoselective Synthesis of Glycans  [in Japanese]

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Abstract

1,2-<i>cis</i> Glycosidic linkages are prevalent in natural glycans. Although key factors that control stereoselectivity of glycosylation have been largely understood, stereoselective synthesis of 1,2-<i>cis</i> glycosides is potentially problematic. To achieve exclusive formation of desired isomer, approaches based on intramolecular aglycon delivery (IAD) are of special promise. In the last two decades, various mixed acetal linkages and a number of glycosyl donor moieties have been making much progress to develop novel IAD strategies, mainly based on formation of the acetal linkages.<br>The methodology toward the strereoselective 1,2-<i>cis</i> glycosylation using naphthylmethyl (NAP) ether-mediated IAD has been developed. Namely, 2-<i>O</i>-NAP protected donor was cleanly converted to the mixed acetal upon oxidative activation with DDQ. Subsequent activation of thioglycosidic linkage initiated the rearrangement of an aglycon from mixed acetal moiety to give a desired 1,2-<i>cis</i> glycoside. Stereospecific constructions of various 1,2-<i>cis</i> linkages, which are not only β-mannopyranoside but also other linkages such as β-L-rhamno-, α-glucopyrano- and β-arabinofurano-sides, were achieved through NAP-IAD. This methodology was successfully applied to the synthesis of various fragments of natural glycans.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 70(4), 382-394, 2012-04-01

    The Society of Synthetic Organic Chemistry, Japan

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Codes

  • NII Article ID (NAID)
    10030576919
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    ART
  • ISSN
    00379980
  • NDL Article ID
    023664832
  • NDL Call No.
    Z17-256
  • Data Source
    CJP  NDL  J-STAGE 
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