Nucleophilic displacement reactions in carbohydrates. Part VI. The solvolysis of methyl 2,3-di-O-benzyl-6-O-methylsulphonyl-β-D-galactopyranoside: participation by a benzyloxy-group

doi:10.1039/J39680001642

Paper

Nucleophilic displacement reactions in carbohydrates. Part VI. The solvolysis of methyl 2,3-di-O-benzyl-6-O-methylsulphonyl-β-D-galactopyranoside: participation by a benzyloxy-group

Published 1968 · J. S. Brimacombe, O. A. Ching

Journal of The Chemical Society C: Organic

UNKNOWN SJR score

4

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Abstract

Product analysis indicates that the 3-benzyloxy-group participates in the solvolysis of methyl 2,3-di-O-benzyl-6-O-methylsulphonyl-β-D-galactopyranoside in either buffered aqueous methanol or NN-dimethylformamide. The product of solvolysis is methyl 3,6-anhydro-2-O-benzyl-β-D-galactopyranoside. This anhydro-sugar is also formed on brief treatment of methyl 2-O-benzyl-3,4-O-isopropylidene-6-O-p-tolylsulphonyl-β-D-galactopyranoside with dilute acid, presumably with neighbouring-group participation by the 3-hydroxy-group following removal of the isopropylidene group. Methyl 4,6-O-isopropylidene-β-D-galactopyranoside is formed, together with the 3,4-acetal, on acetonation of methyl β-D-galactopyranoside in the presence of anhydrous copper sulphate.

Study Snapshot

The 3-benzyloxy-group participates in solvolysis of methyl 2,3-di-O-benzyl-6-O-methylsulphonyl--D-galactopyranoside, leading to methyl 3,6-anhydro-2-O-benzyl-

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Nucleophilic displacement reactions in carbohydrates. Part VI. The solvolysis of methyl 2,3-di-O-benzyl-6-O-methylsulphonyl-β-D-galactopyranoside: participation by a benzyloxy-group

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