An Unusual Behavior of Methyl or Benzyl 3-Azido-5-O-Benzoyl-3,6-Di-Deoxy-α-L-Talofuranoside with (Dimethylamino)Sulfur Trifluoride; Migration of the Alkoxyl Group from the C-1 to the C-2 Position
Titel:
An Unusual Behavior of Methyl or Benzyl 3-Azido-5-O-Benzoyl-3,6-Di-Deoxy-α-L-Talofuranoside with (Dimethylamino)Sulfur Trifluoride; Migration of the Alkoxyl Group from the C-1 to the C-2 Position
Auteur:
Hasegawa, Akira Goto, Makoto Kiso, Makoto
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 4 (1985) nr. 4 pagina's 627-638
Jaar:
1985-12-01
Inhoud:
The reaction of methyl or benzyl 3-azido-5-0-benzoyl-3,6-di-deoxy-α-L-talofuranoside with (diethylamino)sulfur trifluoride (DAST) in toluene at 60°C resulted in the formation of 3-azido-5-0-benzoyl-3,6-dideoxy-2-0-methyl (or 2-0-benzyl)-3β-L-galactofuranosyl fluoride in good yield. In this reaction the alkoxyl group at C-1 migrated to the C-2 position and a fluorine atom entered into the C-1 position. The furanosyl fluoride was converted, via reduction of the azido group followed by N-trifluoroacetylation, acetolysis, and O-deacetylation, into 3,6-dideoxy-2-0-methyl-3-trifluoroacet-amido-L-galactopyranose (2-methoxy-Daunosamine derivative).