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

Keywords

  • Cyclic sulfite
  • KDO
  • β-elimination

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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