title: Catalytic stereoselective synthesis of β-digitoxosides: direct synthesis of digitoxin and C1'-epi-digitoxin.
abstract: A mild and atom-economic rhenium(V)-catalyzed stereoselective synthesis of β-D-digitoxosides from 6-deoxy-D-allals has been described. This β-selective glycosylation was achieved probably because of the formation of corresponding α-digitoxosides disfavored by 1,3-diaxial interaction. In addition, this method has been successfully applied to the synthesis of digitoxin trisaccharide glycal for the direct synthesis of digitoxin and C1'-epi-digitoxin.
authors.affiliation: Department of Chemistry and School of Green Chemistry and Engineering, The University of Toledo , 2801 West Bancroft Street, Toledo, Ohio 43606, United States.
authors.forename: Kedar N
authors.initials: KN
authors.lastname: Baryal
authors.forename: Surya
authors.initials: S
authors.lastname: Adhikari
authors.forename: Jianglong
authors.initials: J
authors.lastname: Zhu
mesh_terms: D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002384:Catalysis; D004074:Digitoxin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D013237:Stereoisomerism
chemical_list: D004074:Digitoxin