Direct synthesis of 2-deoxy-β-glycosides via anomeric O-alkylation with secondary electrophiles.
An approach for direct synthesis of biologically significant 2-deoxy-β-glycosides has been developed via O-alkylation of a variety of 2-deoxy-sugar-derived anomeric alkoxides using challenging secondary triflates as electrophiles. It was found a free hydroxyl group at C3 of the 2-deoxy-sugar-derived lactols is required in order to achieve synthetically efficient yields. This method has also been applied to the convergent synthesis of a 2-deoxy-β-tetrasaccharide.
Department of Chemistry and School of Green Chemistry and Engineering, The University of Toledo , 2801 West Bancroft Street, Toledo, Ohio 43606, United States.
Danyang
D
Zhu
Kedar N
KN
Baryal
Surya
S
Adhikari
Jianglong
J
Zhu
D000478:Alkylation; D003837:Deoxy Sugars / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D003837:Deoxy Sugars; D006027:Glycosides