Formation of methyl 2,6-anhydro-3,4-O-isopropylidene-α-and -β-D-talopyranosides by an intramolecular displacement in the methanolysis of 1,6-anhydro-3,4-O-isopropylidene-2-O-methylsulphonyl-β-D-galactopyranose

doi:10.1039/J39690002263

Paper

Formation of methyl 2,6-anhydro-3,4-O-isopropylidene-α-and -β-D-talopyranosides by an intramolecular displacement in the methanolysis of 1,6-anhydro-3,4-O-isopropylidene-2-O-methylsulphonyl-β-D-galactopyranose

Published 1969 · N. A. Hughes

Journal of The Chemical Society C: Organic

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Abstract

Methyl 2,6-anhydro-3,4-O-isopropylidene-α- and -β-D-talopyranosides are formed when 1,6-anhydro-3,4-O-isopropylidene-2-O-methylsulphonyl-β-D-galactopyranose is heated in methanol containing potassium fluoride dihydrate. The reaction apparently proceeds via an intramolecular displacement, for the isomeric 1,6-anhydro-3,4-O-isopropylidene-2-O-methylsulphonyl-β-D-talopyranose is unreactive in displacement reactions. The utility of potassium fluoride in methanol as a non-nucleophilic base is discussed.

Study Snapshot

Methyl 2,6-anhydro-3,4-O-isopropylidene-- and --D-talopyranosides are formed when 1,6-anhydro-3,4-O-isopropylidene-2-O-methylsulphony

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Formation of methyl 2,6-anhydro-3,4-O-isopropylidene-α-and -β-D-talopyranosides by an intramolecular displacement in the methanolysis of 1,6-anhydro-3,4-O-isopropylidene-2-O-methylsulphonyl-β-D-galactopyranose

References

Citations

Skeletal rearrangements resulting from reactions of 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses with diethylaminosulphur trifluoride.

Reactions of 1,6:2,3- and 1,6:3,4-dianhydro--D-hexopyranoses with diethylaminosulphur trifluoride lead to skeletal rearrangements, with most products resulting from nucleophilic substitution and minor products from migration or

Chemistry of anhydro sugars.

Anhydro sugars are versatile starting materials for synthesis of noncarbohydrate and nonnatural compounds, with their reactivity mainly determined by the size of oxygen rings.

1,6-Anhydro Derivatives of Aldohexoses

1,6-anhydroaldohexopyranoses and 1,6-anhydroaldohexofuranoses are aldohexose derivatives with steric rigidity, useful in synthesis of hexoses, oligosaccharides, and