title: The de novo synthesis of oligosaccharides: application to the medicinal chemistry SAR-study of digitoxin.
abstract: To address the medicinal chemist's need for new synthetic methods for the preparation of unnatural carbohydrates, a new de novo method for carbohydrate synthesis has been developed. These routes use a palladium catalyzed glycosylation reaction to stereoselectively control the anomeric center and subsequent diastereoselective post glycosylation to install the remaining sugar stereocenters. The utility of this method was demonstrated by the syntheses and biological evaluation of several digitoxin oligosaccharide analogues.
authors.affiliation: Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
authors.forename: Maoquan
authors.initials: M
authors.lastname: Zhou
authors.forename: George
authors.initials: G
authors.lastname: O'Doherty
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects; D002626:Chemistry, Pharmaceutical; D004074:Digitoxin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D009844:Oligosaccharides; D004074:Digitoxin