Stereoselective Synthesis of S-Linked Hexasaccharide of Landomycin A via Umpolung S-Glycosylation.
Stereoselective synthesis of carbohydrate mimics resistant toward acid-mediated or enzymatic hydrolysis is chemically challenging and biologically interesting. In this Letter, the first stereoselective synthesis of a "non-hydrolyzable" S-linked hexasaccharide of antitumor antibiotic landomycin A is described. This synthesis was accomplished through the utilization of our recently developed umpolung reactivity-based S-glycosylation-sulfenylation of stereochemically defined glycosyl lithium species with asymmetric sugar-derived disulfides.
Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo , 2801 West Bancroft Street, Toledo, Ohio 43606, United States.
Kedar N
KN
Baryal
Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo , 2801 West Bancroft Street, Toledo, Ohio 43606, United States.
Jianglong
J
Zhu
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry; D013329:Structure-Activity Relationship
D000617:Aminoglycosides; D000903:Antibiotics, Antineoplastic; C064648:landomycin A