Concise synthesis of 3-deoxy-D-manno-oct-2-ulosonic acid (KDO) as a protected form based on a new transformation of α,β-unsaturated ester to α-oxocarboxylic acid ester via diol cyclic sulfite

Atsuhito Kuboki, Toshihiro Tajimi, Yoshihide Tokuda, Dai Ichiro Kato, Takeshi Sugai, Susumu Ohira

研究成果: Article査読

17 被引用数 (Scopus)

抄録

A concise synthesis of KDO (1) as the suitably protected form (2) from 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (3) was achieved in five steps (overall 65% yield). The key step is the efficient transformation of readily available α,β-unsaturated ester to α-oxocarboxylic acid ester. The newly β-elimination of the corresponding diol cyclic sulfite and the in situ trap (DBU/TMSCl) into enol silyl ether was developed to give the tautomeric equivalent of α-oxocarboxylic acid ester. The deprotection of acid labile TMS ether provided the desired product.

本文言語English
ページ(範囲)4545-4548
ページ数4
ジャーナルTetrahedron Letters
45
23
DOI
出版ステータスPublished - 2004 5月 31

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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「Concise synthesis of 3-deoxy-D-manno-oct-2-ulosonic acid (KDO) as a protected form based on a new transformation of α,β-unsaturated ester to α-oxocarboxylic acid ester via diol cyclic sulfite」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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