title: Unusually Stable Picoloyl-Protected Trimethylsilyl Glycosides for Nonsymmetrical 1,1'-Glycosylation and Synthesis of 1,1'-Disaccharides with Diverse Configurations.
abstract: Nonsymmetrical 1,1'-disaccharides and related derivatives constitute structural components in various glycolipids and natural products. Some of these compounds have been shown to exhibit appealing biological properties. We report a direct yet stereoselective 1,1'-glycosylation strategy for the synthesis of nonsymmetrical 1,1'-disaccharides with diverse configurations and sugar components. The strategy is based on the joined forces of a new class of configurationally stable glycoside acceptors and stereodirecting thioglycoside donors. The new glycoside acceptors feature a picoloyl (Pico) protecting group at the remote C4/C3 position that confers unusual stability on TMS glycosides under acidic conditions.
authors.affiliation: Applied Chemistry Department, National Chiao Tung University, 1001, University Road, Hisnchu City, Taiwan, R.O.C.
authors.forename: Yen-Chu Luke
authors.initials: YL
authors.lastname: Lu
authors.affiliation: Applied Chemistry Department, National Chiao Tung University, 1001, University Road, Hisnchu City, Taiwan, R.O.C.
authors.forename: Bhaswati
authors.initials: B
authors.lastname: Ghosh
authors.affiliation: Applied Chemistry Department, National Chiao Tung University, 1001, University Road, Hisnchu City, Taiwan, R.O.C.
authors.forename: Kwok-Kong Tony
authors.identifier: http://orcid.org/0000-0002-5787-1072
authors.initials: KT
authors.lastname: Mong
mesh_terms: D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D004187:Disaccharides; D006027:Glycosides
keywords: carbohydrates; donor-acceptor systems; glycosides; glycosylation; protecting groups