Synthesis and antioxidant activity of a novel class of 4,6-O-protected O-glycosides and their utility in disaccharide synthesis.
BF(3).Et(2)O-catalysed O-glycosylation of 1,2,3-tri-O-acetyl-4,6-O-butylidene- and ethylidene-beta-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) approximately 77%). 1,3-Dipolar cycloaddition of terminal alkyne derivatives of O-glycosides with glycosyl azide results in disaccharides.
Rajaganesh
Ramanathan
R
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
Jayakumar
Jayaraman
J
Sivaraj
Chandrasekaran
C
Raaman
Nanjian
N
Das
Thangamuthu Mohan
TM
D000438:Alcohols / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D001880:Boranes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005027:Ethylene Oxide / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D008968:Molecular Conformation; D013237:Stereoisomerism
D000438:Alcohols; D000480:Alkynes; D000975:Antioxidants; D001386:Azides; D001880:Boranes; D004187:Disaccharides; D006027:Glycosides; C021274:boron trifluoride; D005027:Ethylene Oxide