Synthetic receptor analogues: preparation of the 3-O-methyl, 3-C-methyl, and 3-deoxy derivatives of methyl 4-O-α-d-galactopyranosyl-β-d-galactopyranoside (methyl β-d-galabioside)

Add time:09/25/2019    Source:sciencedirect.com

Methyl β-d-galactopyranoside was transformed into methyl 2-O-benzyl- (5, 24%) and 2-O-benzyloxymethyl-4,6-O-benzylidene-β-d-galactopyranoside (8, 60%) in two and four steps respectively. Compounds 5 and 8 were then transformed into the corresponding 3-O-methyl, 3-C-methyl, and 3-deoxy derivatives variously by O-methylation, Wittig olefination/stereospecific hydrogenation, and xanthate reduction. Regioselective reductive opening of the 4,6-O-benzylidene rings gave galactoside derivatives with HO-4 unsubstituted. Bromide-ion catalysed α-d-galactosidation and hydrogenolysis of the benzyl protecting-groups then gave the desired β-d-galabioside analogues.

We also recommend Trading Suppliers and Manufacturers of Benzyl β-D-galactopyranoside 6-benzoate (cas 16741-14-3). Pls Click Website Link as below: cas 16741-14-3 suppliers

Prev:The conversion of benzyl 3-O-benzoyl-4,6-O-benzylidene-β-d-galactopyranoside into the 2-benzoate by acyl migration
Next:Syntheses of 3-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-α-d-galactopyranose (“lacto-N-biose II”) and 3,4-di-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-d-galactopyranose)