Stereoselective Synthesis of α‐3‐Deoxy‐D‐manno‐oct‐2‐ulosonic Acid (α‐Kdo) Glycosides Using 5,7‐O‐Di‐tert‐butylsilylene‐Protected Kdo Ethyl Thioglycoside Donors |
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| Authors: | Jia‐Sheng Huang Wei Huang Xue Meng Xin Wang Peng‐Cheng Gao Prof. Dr. Jin‐Song Yang |
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| Affiliation: | 1. Department of Chemistry of Medicinal Natural Products, Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy;2. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China) |
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| Abstract: | An efficient methodology for the synthesis of α‐Kdo glycosidic bonds has been developed with 5,7‐O‐di‐tert‐butylsilylene (DTBS) protected Kdo ethyl thioglycosides as glycosyl donors. The approach permits a wide scope of acceptors to be used, thus affording biologically significant Kdo glycosides in good to excellent chemical yields with complete α‐selectivity. The synthetic utility of an orthogonally protected Kdo donor has been demonstrated by concise preparation of two α‐Kdo‐containing oligosaccharides. |
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| Keywords: | acetals carbohydrates glycosylation silanes synthesis design |
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