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

…, MH Burzynska, RM Ratcliffe

Index: Lemieux, R. U.; Abbas, S. Z.; Burzynska, M. H.; Ratcliffe, R. M. Canadian Journal of Chemistry, 1982 , vol. 60, p. 63 - 67

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Citation Number: 50

Abstract

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 cerie ammonium nitrate and sodium azide and ...