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

DOI Web Site 被引用文献5件 参考文献208件
  • 石渡 明弘
    独立行政法人理化学研究所·基幹研究所
  • 伊藤 幸成
    独立行政法人理化学研究所·基幹研究所 ERATO伊藤グライコトリロジープロジェクト·科学技振興事業団

書誌事項

タイトル別名
  • Intramolecular Aglycon Delivery and Its Application to Stereoselective Synthesis of Glycans
  • ブンシ ナイ アグリコン テンイ ハンノウ ト リッタイ センタクテキ トウ サ ゴウセイ エ ノ オウヨウ

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抄録

1,2-cis Glycosidic linkages are prevalent in natural glycans. Although key factors that control stereoselectivity of glycosylation have been largely understood, stereoselective synthesis of 1,2-cis 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-cis glycosylation using naphthylmethyl (NAP) ether-mediated IAD has been developed. Namely, 2-O-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-cis glycoside. Stereospecific constructions of various 1,2-cis 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.

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