FeCl3-catalyzed alpha-glycosidation of glycosamine pentaacetates.
An efficient method for the large-scale preparation of alpha-N-acetylglycosaminides, such as fluorogenic T(N)-antigen probes and an alpha-GalNAc-Ser derivative, has been achieved using FeCl(3)-catalyzed one-step condensation between commercially available D-glycosamine pentaacetates and fluorogenic acceptors (or serine acceptor) in refluxing 1,2-dichloroethane. Experimental simplicity, high alpha-stereoselectivity, low cost, satisfactory yield, and the environmentally benign nature are major advantages of our approach.
Wei
Guohua
G
State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Scienece, Chinese Academy of Sciences, Beijing 100085, China.
Lv
Xun
X
Du
Yuguo
Y
D000117:Acetylglucosamine / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides; D003365:Costs and Cost Analysis; D005290:Ferric Compounds / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D055772:Green Chemistry Technology; D013237:Stereoisomerism; D013379:Substrate Specificity
D002712:Chlorides; D005290:Ferric Compounds; D006027:Glycosides; C024555:ferric chloride; D000117:Acetylglucosamine