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- 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.
- Authors
Huang, Jia‐Sheng; Huang, Wei; Meng, Xue; Wang, Xin; Gao, Peng‐Cheng; Yang, Jin‐Song
- 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.
- Subjects
STEREOSELECTIVE reactions; CHEMICAL synthesis; GLYCOSIDE synthesis; ETHYL chloride; OLIGOSACCHARIDES
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 37, p10894
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201505176