Synthesis and characterization of methyl 6-O-β-d-galactopyranosyl-β-d-galactopyranoside and methyl O-β-d-galactopyranosyl-(1→6)-O-β-d-galactopyranosyl-(1→6)-β-d-galactopyranoside☆

Add time:09/08/2019    Source:sciencedirect.com

6-O-Acetyl-2-O-benzoyl-3,4-di-O-benzyl-α-d-galactopyranosyl chloride (8) was prepared from 1,6-anhydro-2-O-benzoyl-3,4-di-O-benzyl-β-d-galactopyranose via the corresponding 1,6-di-O-acetyl derivative 7. The glycosyl chloride 8 was converted into the 1-O-tosyl derivative (9) which was allowed to react with methanol in acetonitrile to form methyl 6-O-acetyl-2-O-benzoyl-3,4-di-O-benzyl-β-d-galactopyranoside (10). Compound 10 was O-deacetylated with ammonium hydroxide in methanol to give 11. Reaction of 9 with 11 under the same conditions of glycosidation gave the corresponding disaccharide derivative 12. O-Deacetylation of 12 followed by glycosidation with 9 gave the corresponding trisaccharide derivative 16. Appropriate deblocking sequences gave the title compounds. The structures of the glycosides were determined with the aid of both 1H- and 13C-n.m.r. spectroscopy. No evidence of α-d linkages was found.

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