Stereoselective synthesis of aryl 1,2-cis-furanosides and its application to the synthesis of the carbohydrate portion of antibiotic hygromycin A

• Published in: Tetrahedron letters Vol. 58; no. 16; pp. 1548 - 1552
• Main Authors: Xu, Yuan, Bin, Hua-Chao, Su, Fu, Yang, Jin-Song
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 19.04.2017; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Furanoside; Glycosylation; Hygromycin A; Physical Sciences; Science & Technology; Stereoselectivity; Synthesis; Thioglycoside; Stereoselectivity; Glycosylation; Furanoside; Synthesis; Hygromycin A; Thioglycoside; OXIDATION; HOMOMYCIN; A201A; RELEVANT; AMINOCYCLITOL ANALOGS; GLYCOSYL DONORS; ANTIBACTERIAL ACTIVITY; SEMISYNTHETIC MODIFICATION; NUCLEOSIDE ANTIBIOTICS; A SYNTHESIS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2017.02.079

[Display omitted] •A approach to the construction of aryl 1,2-cis-furanosidic bonds is developed.•Aryl 1,2-cis-furanosides are synthesized using Quin-substituted thiofuranosides.•The method is demonstrated by preparation of the sugar portion of hygromycin A. An efficient methodology for the synthesis of aryl 1,2-cis-furanosidic linkages has been developed with 2-quinolinecarbonyl (Quin) group substituted furanose ethyl thioglycosides as glycosyl donors. The method permits a wide range of phenol acceptors to be used, thus resulting in the formation of structurally diverse phenol furanosides in good to excellent chemical yields with complete 1,2-cis anomeric selectivity. The synthetic utility of the approach has been demonstrated by concise preparation of the carbohydrate portion of antibiotic hygromycin A.