title: Synthesis of the 2-deoxy trisaccharide glycal of antitumor antibiotics landomycins A and E.
abstract: Synthesis of the 2-deoxy trisaccharide glycal of antitumor antibiotics landomycins A and E has been described. The synthesis involves an anomeric O-alkylation for the synthesis of 2-deoxy β-linked disaccharide, a tert-butyldimethylsilyl triflate-catalyzed α-selective L-rhodinosylation, and a lithium 4,4'-di-tert-butylbiphenyl-mediated reductive debenzylation and concomitant reductive lithiation-elimination for the production of the 2-deoxy trisaccharide glycal.
authors.affiliation: Department of Natural Sciences, University of Michigan-Dearborn, 4901 Evergreen Road, Dearborn, Michigan 48128, United States. Electronic address: shannli@umich.edu.
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Li
authors.affiliation: Department of Natural Sciences, University of Michigan-Dearborn, 4901 Evergreen Road, Dearborn, Michigan 48128, United States.
authors.forename: Justin
authors.initials: J
authors.lastname: Woodward
authors.affiliation: Department of Natural Sciences, University of Michigan-Dearborn, 4901 Evergreen Road, Dearborn, Michigan 48128, United States.
authors.forename: Ali
authors.initials: A
authors.lastname: Hourani
authors.affiliation: Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, United States.
authors.forename: Danyang
authors.initials: D
authors.lastname: Zhu
authors.affiliation: Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, United States.
authors.forename: Sabrine
authors.initials: S
authors.lastname: Ayoub
authors.affiliation: Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, United States. Electronic address: Jianglong.Zhu@Utoledo.edu.
authors.forename: Jianglong
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000478:Alkylation; D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D014312:Trisaccharides / Q000737:chemistry*
chemical_list: D000617:Aminoglycosides; D000903:Antibiotics, Antineoplastic; D014312:Trisaccharides; C113593:landomycin E; C064648:landomycin A
keywords: 2-Deoxy sugars; Anomeric O-alkylation; Glycal; Glycosylation