REACTIONS OF D-GLUCOSE, D-XYLOSE, AND D-ERITHROSE WITH 2-METHYL-2-PROPANETHIOL

Article abstract of DOI:10.1016/0008-6215(87)80162-3

The reaction of D-glucose and D-xylose with 2-methyl-2-propanethiol in conc. hydrochloric acid yielded tert-butyl 1-thioglycopyranosides (produts of kinetic and thermodynamic control).Di-tert-butyl dithioacetals (12-14) were obtained from the acetylated aldehydo-derivatives of D-glucose, D-xylose, and D-erythrose.On brief treatment with conc. hydrochloric acid, 12 and 13 gave tert-butyl 1-thio-α- and -β-glycopyranosides and 14 gave the corresponding furanosides.