title: 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.
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.
authors.affiliation: 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.|State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China).
authors.forename: Jia-Sheng
authors.initials: JS
authors.lastname: Huang
authors.affiliation: 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.|State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China).
authors.forename: Wei
authors.initials: W
authors.lastname: Huang
authors.affiliation: 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.|State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China).
authors.forename: Xue
authors.initials: X
authors.lastname: Meng
authors.affiliation: 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.|State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China).
authors.forename: Xin
authors.initials: X
authors.lastname: Wang
authors.affiliation: 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.|State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China).
authors.forename: Peng-Cheng
authors.initials: PC
authors.lastname: Gao
authors.affiliation: 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. yjs@scu.edu.cn.|State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China). yjs@scu.edu.cn.
authors.forename: Jin-Song
authors.initials: JS
authors.lastname: Yang
mesh_terms: D002073:Butanes / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D002073:Butanes; D006027:Glycosides; D009844:Oligosaccharides; D012821:Silanes; D013865:Thioglycosides; C512229:di-tert-butylsilylene
keywords: acetals; carbohydrates; glycosylation; silanes; synthesis design