Bromodimethylsulfonium bromide (BDMS) mediated dithioacetalization of carbohydrates under solvent-free conditions.
A variety of diethyl dithioacetals of sugars can be prepared in very good yields by the reaction of various monosaccharides with ethanethiol in the presence of 3 mol% bromodimethylsulfonium bromide (BDMS) at 0-5°C. Similarly, dipropyl dithioacetal derivatives can also be obtained in good yields using propanethiol under identical reaction conditions. These dithioacetal derivatives were characterized by per-O-acetylation using silica gel-supported perchloric acid. The significant features of the present protocol are good-to-excellent yields, mild, clean, and solvent-free reaction conditions. This method is extremely suitable for the large-scale preparation of dithioacetal derivatives of various sugars.
Khan
Abu T
AT
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781 039, Assam, India. atk@iitg.ernet.in
Khan
Md Musawwer
MM
D001965:Bromides / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry
D001965:Bromides; D002241:Carbohydrates; D012997:Solvents; D013438:Sulfhydryl Compounds; C030762:propanethiol; C007638:ethanethiol