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Stereoselective diversity-oriented syntheses of functionalized saccharides from bicyclic carbohydrate 1,2-lactones

  • Bicyclic carbohydrate 1,2-lactones have been synthesized in only two steps and high yields by saponification and subsequent cyclization from known malonate addition products to glycals. The gluco-configured lactone serves as an important precursor for diversity-oriented syntheses. Thus, stereoselective opening of the lactone ring was realized with various nucleophiles in the presence of Sc(OTf)(3). This enabled the introduction of different substituents at the anomeric position, to afford a broad variety of 1-functionalized carbohydrates. On the other hand, stereoselective alpha-substitution of the gluco-configured lactone with different electrophiles and subsequent ring opening gives a collection of 2-functionalized saccharides. More than 30 products have been isolated in analytically pure form, and their configurations were unequivocally established by various NMR methods. Thus, carbohydrate 1,2-lactones are attractive precursors for the stereoselective synthesis of diverse saccharides.

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Metadaten
Author:Jian Yin, Torsten LinkerORCiDGND
DOI:https://doi.org/10.1016/j.tet.2011.01.069
ISSN:0040-4020 (print)
Parent Title (English):Tetrahedron
Publisher:Elsevier
Place of publication:Oxford
Document Type:Article
Language:English
Year of first Publication:2011
Year of Completion:2011
Release Date:2017/03/26
Tag:Carbohydrates; Glycosides; Lactones; Molecular diversity; Synthetic methods
Volume:67
Issue:13
Pagenumber:15
First Page:2447
Last Page:2461
Funder:Deutsche Forschungsgemeinschaft [Li 556/7-3]; University of Potsdam
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert