title: An efficient synthesis of the protected carbohydrate moiety of Brasilicardin A.
abstract: A synthesis of the protected carbohydrate moiety 2 of Brasilicardin A starting from l-rhamnose and d-glucosamine is described. The disaccharide was synthesized using a TMSOTf-mediated glycosylation of the 2-phthalimido-2-deoxyglucose donor 5 and the 3-hydroxyl group of the protected L-rhamnose derivative 4, which already bears the 3-hydroxybenzoate unit. The imidate 2 was coupled via TMSOTf-mediated glycosidation with cholesterol as a model aglycone followed by the selective cleavage of all the acetate groups to give the Brasilicardin A analogue 16.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA. jung@chem.ucla.edu
authors.forename: Michael E
authors.initials: ME
authors.lastname: Jung
authors.forename: Pierre
authors.initials: P
authors.lastname: Koch
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005944:Glucosamine / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D012210:Rhamnose / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000617:Aminoglycosides; C118259:brasilicardin A; D005944:Glucosamine; D012210:Rhamnose