Convenient preparation of thioglycomimetics: S-glycosyl sulfenamides, sulfinamides and sulphonamides. Issue 52 (27th June 2017)

• Record Type: Journal Article
• Authors: Gucchait, Arin; Jana, Kuladip; Misra, Anup Kumar
• Is Part Of: RSC advances. Volume 7:Issue 52(2017)
• Page Start: 32478
• Page End: 32487
• Publication Date: 2017-06-27
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7ra05339h
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : S -Glycosyl sulfenamide derivatives were rapidly prepared from glycosyl thiols using N -bromosuccinimide or N -chlorosuccinimide. Sulfenamide derivatives were oxidized to corresponding sulfinamides and sulfonamides. Abstract : A series of S -glycosyl sulfenamide derivatives has been prepared in good yield from glycosyl thiols using N -bromosuccinimide (NBS) or N -chlorosuccinimide (NCS) as activator under significantly fast reaction conditions avoiding the use of hazardous reagents. Controlled and complete oxidation of the sulfenamide derivatives under mild reaction conditions led to the formation of the corresponding sulfinamides and sulfonamides in excellent yield.