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

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4545-4548
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number23
DOIs
Publication statusPublished - 2004 May 31

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Sulfites
Esters
Ether
Acids
2-keto-3-deoxyoctonate

Keywords

  • β-elimination
  • Cyclic sulfite
  • KDO

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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

In: Tetrahedron Letters, Vol. 45, No. 23, 31.05.2004, p. 4545-4548.

Research output: Contribution to journalArticle

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AU - Kuboki, Atsuhito

AU - Tajimi, Toshihiro

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AU - Sugai, Takeshi

AU - Ohira, Susumu

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