L. A. Reed, L. Goodman
Jul 16, 1981
Citations
0
Influential Citations
28
Citations
Journal
Carbohydrate Research
Abstract
Abstract The potential enzyme inducer, 4- S -β- d -galactopyranosyl-4-thio- d -glucopyranose, thiolactose ( 20 ), was synthesized via two routes. The intermediate, methyl 2,3,6-trio- O -benzoyl-4- S -cyano-4-thio-α- d -glucopyranoside ( 5 ), was obtained in high yield from methyl α- d -galactopyranoside. Reaction of the sodium salt of methyl 4-thio-α- d -glucopyranoside, derived from 5 , with 2,3,4,6-tetra- O -acetyl-α- d -galactopyranosyl bromide in hexamethylphosphoric triamide produced a methyl thiolactoside derivative that could be selectively benzoylated to give 2,6,-di- O -benzoyl- S -(2,3,4,6-tetra- O -acetyl-β- d -galactopyranosyl)-4-thio-α- d -glucopyranoside ( 14 ), which was directly crystallized from a complex mixture of products produced in the coupling reaction. Selective acetolysis of the methyl glycoside linkage of 14 (or of the derived heptaacetate), followed by transesterification, afforded 20 .