Syntheses of derivatives of N-acetyl-D-lactosamine from D-lactal hexaacetate. Hexa-O-acetyl-2-deoxy-2-phthalimido-β-D-lactosyl chloride
- 1 January 1982
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 60 (1), 63-67
- https://doi.org/10.1139/v82-011
Abstract
Two reaction routes are presented for the preparation of hexa-O-acetyl-2-deoxy-2-phthalimido-.beta.-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-2-.alpha.-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 .beta.-anomer of 4 as an intermediate. The preparation of 7 is of interest as a reagent for the preparation of 2-amino-2-deoxy-.beta.-D-lactosides. The procedures offer routes for the preparation of D-lactosamine.This publication has 5 references indexed in Scilit:
- Syntheses of derivatives of lacto-N-biose. I. 4,6-Di-O-acetyl-3-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-α,β-D-glucopyranosyl chlorideCanadian Journal of Chemistry, 1982
- Immunochemical studies on blood groups—LXIX. The conformation of the trisaccharide determinant in the combining site of anti-I Ma (group 1)Molecular Immunology, 1981
- The azidonitration of tri-O-acetyl-D-galactalCanadian Journal of Chemistry, 1979
- Synthesis of 2-Amino-2-deoxy-β-D-glucopyranosidesPublished by American Chemical Society (ACS) ,1977
- Immunochemical studies on blood groups. XXXVIII. Structures and activities of oligosaccharides produced by alkaline degradation of blood-group Lewisa substance. Proposed structure of the carbohydrate chains of human blood-group A,B,H,Lea, and Leb substancesBiochemistry, 1968