Synthesis of O-[4,6-Di-O-Acetyl-4-O-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)-2-Deoxy-2-Hydroxyimino-D-Arabino-Hexopyranosyl]-N-Benzyloxycarbonyl-L-Serine Methyl Esters And Their Transformations

ABSTRACT

3,6-Di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-hydroxyimino-α- and -β-D-arabino-hexopyranosides of N-benzyloxycarbonyl-L-serine methyl ester as well as of ethanol have been synthesised from D-lactal hexaacetate via nitrosyl chloride, followed by condensation with L-serine derivatives and ethanol, respectively. The compounds of L-serine thus obtained were modified at C-2 and C-3 to afford L-serine derivatives attached to disaccharides containing terminal α-D-gluco-, 2-acetamido-α-D-gluco-, β-D-manno, 2-acetamido-β-D-manno-pyranosyl, 3-azido-2-hydroxyimino-α-D-arabino-, and α-D-ribo-hexopyranosyl residues.