Syntheses of derivatives of N-acetyl-D-lactosamine from D-lactal hexaacetate. Hexa-O-acetyl-2-deoxy-2-phthalimido-β-D-lactosyl chloride

Article abstract of DOI:10.1139/v82-011

Two reaction routes are presented for the preparation of hexa-O-acetyl-2-deoxy-2-phthalimido-β-D-lactosyl chloride (7) from lactal hexaacetate (1).One route involves, in the first stage, reaction of 1 with nitrosyl chloride and proceeds by way of benzyl 2-amino-2-deoxy-α-D-lactoside (4) as an intermediate.The other route, which is considered more efficient, involves reaction of 1 with ceric ammonium nitrate and sodium azide and involves the β-anomer (12) of 4 as an intermediate.The preparation of 7 is of interest as a reagent for the preparation of 2-amino-2-deoxy-β-D-lactosides.The procedures offer routes for the preparation of D-lactosamine.