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.
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