Verfahren zur Herstellung von 6-Azido-2,4-Diacetamido-2,4,6-Trideoxy-D-Mannose

Details

Veröffentlichungs-Nr.

EP3170832

Aktenzeichen

EP15306825

Anmeldetag

17. November 2015

Veröffentlichung

24. Mai 2017

Rechtsraum

EP

IPC

C07H5/06C12Q1/04G01N33/58

Abstract

The invention relates to a method of preparation of 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose. This method comprises the chemical reaction of compound of formula X: Wherein: R 1 can be a C 1 to C 6 alkyl including methyl, ethyl, isopropyl; aryl including phenyl; each of these groups being substituted or not; and R 2 can be a C 1 to C 6 alkyl including methyl, ethyl, isopropyl, tert -butyl, isobutyl; each of these groups being substituted or not; with a deprotecting reagent comprising a Lewis or Brönsted acid in a polar aprotic solvent, thereby obtaining a free C-1 OH group. The method can also start with the preparation from commercially available D-galactose pentaacetate, D-galactose tetraacetate or tetraacetyl D-galactosyl trichloroacetimidate. According to the invention the step of deprotecting the anomeric position avoids the use of cerium and allows the easy purification of 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose.

Anmelder

Firma

Centre National de la Recherche Scientifique

Land

🇫🇷 Frankreich

Fachgebiete