Regio- and chemoselective manipulation under mild conditions on glucosamine derivatives for oligosaccharide synthesis and its application toward N-acetyl-d-lactosamine and Lewis X trisaccharide

Yasuhito Nagai, Naoyuki Ito, Israt Sultana, Takeshi Sugai

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Special emphasis on regio- and chemoselective manipulation on a new glucosamine scaffold was laid, toward the short-step and efficient synthetic routes for oligosaccharides. First, the blocking of two hydroxyl groups at C-1 and C-6 positions of N-protected glucosamine at once by silylation followed by an oxazolidinone formation between C-3 hydroxyl and C-2 amino groups were established, to lead an expeditious way for a glycosyl acceptor for lactosamine synthesis. Second, without any effect on acetyl protective groups in the same molecule, the ring-opening of oxazolidinone and hydrolysis of resulting carbonate under mild conditions allowed the C-3 hydroxyl group to be free, which is indispensable for further extension to oligosaccharides, such as a LeX trisaccharide.

Original languageEnglish
Pages (from-to)9599-9606
Number of pages8
JournalTetrahedron
Volume64
Issue number40
DOIs
Publication statusPublished - 2008 Sep 29

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Glucosamine
Oligosaccharides
Hydroxyl Radical
Oxazolidinones
Derivatives
Trisaccharides
Carbonates
Scaffolds
Hydrolysis
Molecules
galactosyl-(1,4)-fucopyranosyl-(1,3)-N-acetylglucosamine
lactosamine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Regio- and chemoselective manipulation under mild conditions on glucosamine derivatives for oligosaccharide synthesis and its application toward N-acetyl-d-lactosamine and Lewis X trisaccharide. / Nagai, Yasuhito; Ito, Naoyuki; Sultana, Israt; Sugai, Takeshi.

In: Tetrahedron, Vol. 64, No. 40, 29.09.2008, p. 9599-9606.

Research output: Contribution to journalArticle

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