The synthesis of 2-O-α-d-galactopyranosyl-d-galactopyranose and 2-O-(2-O-α-d-galactopyranosyl-α-d-galactopyranosyl)-d-glucopyranose undeca-acetate
✍ Scribed by Bogdan Doboszewski; Aleksander Zamojski
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- English
- Weight
- 714 KB
- Volume
- 132
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
The synthesis of 2-~-cY-D-galaCtOpyranOSyl-D-galaCtOpyranOSC was accomplished by condensation of 2,3,4.6-tetra-0-benzyl-a-D-galactopyranosyl chloride with 2,2,2-trichloroethyl 3,4,6-tri-O-benzyl-a-D-galactopyranoside in the presence of mercuric cyanide. The title trisaccharide undeca-acetate was prepared by condensing 1 ,3,4,6-tetra-O-acety1-2-0-(3,4,6-tri-O-acetyl-cY-D-galactopyranosyl)-a-D-ghrcopyranose with 2,3,4,6-tetra-0-benzyl-a-D-galactopyranosyl chloride or bromide in the presence of various glycosidation catalysts, followed by debenzylation and acetylation.
📜 SIMILAR VOLUMES
The title trisaccharide glycosides were needed for studies of the interactions of &tins, receptor sites for bacteriophages with Salmonella lipopolysaccharide corespecificity, and correlation of n.m.r. chemical shifts and structure. The methods used in the syntheses were conventional. Thus, 2,3,4,6-
Ally1 4-0-(4-O-acetyl-2-O-benzoyl-3,6-di-O-benzyl-~-D-galactopyranosyl)-2-0-benzoyl-3,6-di-O-benzyl-a-D-galactopyranoside was 0-deallylated to give the 1-hydroxy derivative, and this was converted into the corresponding l-O-(Nphenylcarbamoyl) derivative, treatment of which with dry HCl produced the