Stereoselective synthesis of oligo-α(2,8)-3-deoxy-D-manno-2- octulosonic acid derivatives

Hiroshi Tanaka, Daisuke Takahashi, Takashi Takahashi

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

(Chemical Equation Presented) Iodoalkoxylation (see scheme) of a glycal with an acyclic saccharide precursor leads to an efficient stereoselective synthesis of di- and tri-α(2,8)-3-deoxy-D-manno-2-octulosonic acid (KDO; see picture). The glycal forms α-linked 3-iodo-KDO derivatives. The opening of the pyran ring improves the reactivity of the C8 hydroxy group. NIS = N-iodosuccimide, Tf = triflate, M.S. = molecular sieves.

Original languageEnglish
Pages (from-to)770-773
Number of pages4
JournalAngewandte Chemie - International Edition
Volume45
Issue number5
DOIs
Publication statusPublished - 2006 Jan 23
Externally publishedYes

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Pyrans
Molecular sieves
Derivatives
Acids
3-deoxy-manno-oct-2-ulopyranosonic acid

Keywords

  • Carbohydrates
  • Glycosides
  • Glycosylation
  • Oligosaccharides
  • Synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Stereoselective synthesis of oligo-α(2,8)-3-deoxy-D-manno-2- octulosonic acid derivatives. / Tanaka, Hiroshi; Takahashi, Daisuke; Takahashi, Takashi.

In: Angewandte Chemie - International Edition, Vol. 45, No. 5, 23.01.2006, p. 770-773.

Research output: Contribution to journalArticle

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