Synthesis of 3,6-dideoxy-3-(methylamino)hexoses for g.l.c.-m.s. identification of Rhizobium lipopolysaccharide components.

Academic Article

Abstract

  • A direct synthetic route from methyl alpha-D-glucopyranoside to 3,6-dideoxy-3-(methylamino)hexoses having the D-gluco, D-galacto, and D-manno configurations has been developed. Methyl alpha-D-glucoside was converted into the 4,6-O-benzylidene-2,3-di-O-tosyl derivative, which was then transformed into the 4-O-benzyl-6-deoxy 2,3-ditosylate (5) by successive reductive cleavage of the acetal ring, iodination, and reduction. The intermediate 5 was readily converted into the allo 2,3-epoxide, which yielded the pivotal intermediate methyl 4-O-benzyl-3,6-dideoxy-3-(methylamino)-alpha-D-glucopyranoside (7) by cleavage of the oxirane ring with methylamine. The amino compound 7 can be directly converted into the derivatized galacto and manno derivatives for mass-spectrometric identification by selective inversion at C-4 and C-2, respectively, followed by hydrolysis, reduction, and acetylation.
  • Authors

  • Hollingsworth, RI
  • Hrabak, Estelle
  • Dazzo, FB
  • Status

    Publication Date

  • October 15, 1986
  • Published In

    Keywords

  • Amino Sugars
  • Gas Chromatography-Mass Spectrometry
  • Hexoses
  • Indicators and Reagents
  • Lipopolysaccharides
  • Magnetic Resonance Spectroscopy
  • Optical Rotation
  • Rhizobium
  • Digital Object Identifier (doi)

    Pubmed Id

  • 3791291
  • Start Page

  • 103
  • End Page

  • 113
  • Volume

  • 154
  • Issue

  • 1