Synthesis and antioxidant activity of a novel class of 4,6-O-protected O-glycosides and their utility in disaccharide synthesis

• Published in: Carbohydrate research Vol. 345; no. 12; pp. 1649 - 1657
• Main Authors: Rajaganesh, Ramanathan, Jayakumar, Jayaraman, Sivaraj, Chandrasekaran, Raaman, Nanjian, Das, Thangamuthu Mohan
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 16.08.2010; Elsevier
• Subjects: Alcohols - chemistry; Alkynes - chemistry; Antioxidant activity; Antioxidants - chemical synthesis; Antioxidants - chemistry; Azides - chemistry; Biochemistry & Molecular Biology; Boranes - chemistry; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; Cyclization; Disaccharide; Disaccharides - chemical synthesis; Disaccharides - chemistry; Ethylene Oxide - chemistry; Glycosides - chemical synthesis; Glycosides - chemistry; Glycosylation; Life Sciences & Biomedicine; Molecular Conformation; O-Glycosides; Physical Sciences; Protected sugars; Science & Technology; Stereoisomerism; Triazole; XRD-analysis; Protected sugars; Triazole; O-Glycosides; XRD-analysis; Antioxidant activity; Disaccharide; ALLYL; ONE-POT SYNTHESIS; ANALOGS; CLICK CHEMISTRY; D-GLUCOSE
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2010.04.020

BF 3·Et 2O-catalysed O-glycosylation of 1,2,3-tri- O-acetyl-4,6- O-butylidene- and ethylidene-β- d-glucopyranose with different aliphatic and aromatic alcohols proceeds for the most part with complete retention of anomeric configuration. Antioxidant activity of O-glycosides shows significant inhibition (IC 50 ∼77%). 1,3-Dipolar cycloaddition of terminal alkyne derivatives of O-glycosides with glycosyl azide results in disaccharides.