Syntheses of the methyl 1-deoxy-1-mercapto-D-ribosides and the hydrolysis of methyl 1-deoxy-1-mercapto-α-D-ribopyranoside
- 1 January 1967
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 644-648
- https://doi.org/10.1039/j39670000644
Abstract
Syntheses of the four methyl 1-deoxy-1-mercapto-D-ribosides are described. Displacement of the bromine in 2,3,4-tri-O-benzoyl-1-bromo-1-deoxy-β-D-ribopyranose by sodium methanethiolate in dimethylformamide occurs with inversion of configuration without neighbouring group participation. Anomerisation and ring contraction are shown to accompany hydrolysis when methyl 1-deoxy-1-mercapto-α-D-ribopyranoside is treated with hot dilute acid, this is discussed in terms of present theories on glycoside hydrolysis.Keywords
This publication has 0 references indexed in Scilit: