Synthesis of selenoglycosides and selenium linked disaccharides using reductive cleavage of diselenides. (June 2022)

• Record Type: Journal Article
• Authors: Shit, Pradip; Sahaji, Samim; Misra, Anup Kumar
• Is Part Of: Carbohydrate research. Volume 516(2022)
• Publication Date: 2022-06
• Subjects: Selenoglycoside -- Diselenides -- Hydrazine -- Reduction -- Selenium -- Glycosyl; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2022.108554
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: Reduction of diselenides using a combination of hydrazine monohydrate and potassium hydroxide (KOH) followed by the treatment of the selenolate ions generated in situ with glycosyl halides under a one-pot, two-step phase transfer reaction condition resulted in the formation of beta-selenoglycosides in excellent yield. In addition, selenium linked disaccharide derivatives with beta-glycosidic linkages were also prepared by the reductive cleavage of diglycosyl diselenide derivatives in very good yield. The reaction condition is non-hazardous and high yielding for scaling up. Graphical abstract: Image 1 Highlights: Beta-selenoglycosides and selenium linked disaccharides were synthesized. Cleavage of diselenides was done using hydrazine hydrate and KOH. Diselenides were used as selenium precursors. Stereoselective formation of beta-selenoglycosides was achieved. All reactions were simple, high yielding and suitable for scaling up.