M. Kloosterman, P. Westerduin, J. H. Boom
1986
Citations
0
Influential Citations
4
Citations
Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
4-O-Acetyl-1,6-anhydro-3-O-(4-methoxybenzoyl)-β-D -mannopyranose was converted in two steps into 4-O-acetyl-1,6-anhydro-2-deoxy-2-phthalimido-β-D-glucopyranose. Trimethylsilyl tri-fluoromethanesulphonate-catalysed coupling of 1,6-anhydro-2,3-O-(4-methoxybenzylidene)-β-D-mannopyranose with 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose, followed by treatment with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, afforded the title compound. After triflation, the disaccharide thus obtained was treated with lithium azide or potassium phthalimide to afford 4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D- glucopyranosyl)-1,6-anhydro-2-azido-3-O-(4-methoxy-benzoyl)-2-deoxy -β-D-glucopyranose and 4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D -glucopyranosyl) −1,6-anhydro-2-deoxy-3-O-(4-methoxybenzoyl)-2-phthalimido-β- D-glucopyranose, respectively.