K. Hamacher
Jun 1, 1984
Citations
0
Influential Citations
41
Citations
Journal
Carbohydrate Research
Abstract
Abstract Syntheses of the potential enzyme-inducers thiocellobiose ( 7 ) and thiosophorose ( 11 ) are described. The intermediates methyl 2,3,6-tri- O -benzoyl-4- O -trifluoromethylsulfonyl-α- d -galactopyranoside and 1,3,4,6-tetra- O -acetyl-2- O -trifluoromethylsulfonyl-β- d -mannopyranose were obtained in good yield from methyl α- d -galactopyranoside or 1,3,4,6-tetra- O -acetyl-β- d -mannopyranose. The stereoselective reaction of the triflates with the sodium salt of 2,3,4,6-tetra- O -acetyl-1-thio-β- d -glucopyranose was performed under phase-transfer conditions. Transesterification of methyl 2,3,6-tri- O -benzoyl-4- S -(2,3,4,6-tetra- O -acetyl-β- d -glucopyranosyl)-4-thio-β- d -glucopyranoside (after selective acetolysis) and 1,3,4,6-tetra- O -acetyl-2- S -(2,3,4,6-tetra- O -acetyl-β- d -glucopyranosyl)-2-thio-β- d -glucopyranose afforded 7 and 11 .