Hermans, J. P. G. Elie, C. J. J. van der Marel, G. A. Van Boom, J. H.
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 6 (1987) nr. 3 pagina's 451-462
Jaar:
1987-09-01
Inhoud:
Benzyl-2,4-diacetamido-2,4,6-trideoxy-α(β)-D-galactopyranoside 6c was synthesized from l,6-anhydro-2,3-O-(4-methoxybenzylidene)-β-D-mannopyranose la. The azide group at C-4, which is a precursor for the acetamido function, was introduced by substitution of the 4-O-triflate group with lithium azide. After regioselective oxidative acetal ring opening the other C-2 azide function was obtained by the same substitution procedure. Acetolysis of the 1,6-anhydro bridge and α(β)-coupling with benzyl alcohol gave the 2,4-diazido derivative 4b. After base treatment the azide groups were reduced and subsequently acetylated. Selective protection of the primary hydroxyl by the phenyl thionocar-bonyl group followed by reduction afforded the title compound.