Stereoselective synthesis of aryl 1,2-cis-furanosides and its application to the synthesis of the carbohydrate portion of antibiotic hygromycin A |
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Authors: | Yuan Xu Hua-Chao Bin Fu Su Jin-Song Yang |
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Institution: | Department of Chemistry of Medicinal Natural Products, and Key Laboratory of Drug Targeting, Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, China |
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Abstract: | 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. |
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Keywords: | Furanoside Hygromycin A Glycosylation Synthesis Thioglycoside Stereoselectivity |
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