title: Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates.
abstract: Digitoxin, a clinically important cardiac trisaccharide, was assembled efficiently from digitoxigenin and 3,4-di-O-tert-butyldiphenylsilyl-d-digitoxosyl o-cyclopropylethynylbenzoate in 9 steps and 52% overall yield via alternate glycosylation and protecting group manipulation. The present synthesis showcases the advantage of the gold(I)-catalyzed glycosylation protocol in the synthesis of glycoconjugates containing acid-labile 2-deoxysugar linkages.
authors: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
authors: Yuyong
authors: Y
authors: Ma
authors: Zhongzhen
authors: Z
authors: Li
authors: Hefang
authors: H
authors: Shi
authors: Jian
authors: J
authors: Zhang
authors: Biao
authors: B
authors: Yu
mesh_terms: D001565:Benzoates / Q000737:chemistry*; D002384:Catalysis; D004074:Digitoxin / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D008968:Molecular Conformation
chemical_list: D001565:Benzoates; D006027:Glycosides; D006046:Gold; D004074:Digitoxin