D-glucose diphenyl dithioacetal, phenyl 1-thio-α- D-glucopyranoside, phenyl 1-thio-α- D-glucofuranoside, and some related compounds

Abstract

D-Glucose diphenyl dithioacetal has been prepared for the first time, in a 71% yield, by the action of benzenethiol and concentrated hydrochloric acid on D-glucose. It has been converted by acid into phenyl 1-thio-α- D-glucopyranoside and by mercuric chloride—mercuric oxide into phenyl 1-thio-α- D-glucofuranoside; the ring structures of these thioglucosides were established by reductive desulfurization. The thioglucoside acetates, upon oxidation with hydrogen peroxide in glacial acetic acid, yielded the corresponding α- D-glucopyranosyl and α- D-glucofuranosyl phenyl sulfones. An α- D-glucofuranosyl phenyl sulfoxide could be obtained only in very small yield. Some infrared data on these compounds are included.