Journal article
Total Synthesis of Everninomicin 13,384-1-Part 4: Explorations of Methodology; Stereocontrolled Synthesis of 1,1′-Disaccharides, 1,2-Seleno Migrations in Carbohydrates, and Solution- and Solid-Phase Synthesis of 2-Deoxy Glycosides and Orthoesters
Chemistry : a European journal, Vol.6(17), pp.3166-3185
09/01/2000
DOI: 10.1002/1521-3765(20000901)6:17<3166::AID-CHEM3166>3.0.CO;2-Z
PMID: 11002995
Abstract
Methods for the stereocontrolled construction of 1,1′-disaccharides, 2-deoxy glycosides, and orthoesters are reported. Specifically, a tin-acetal moiety was utilized to fix the anomeric stereochemistry of a carbohydrate acceptor leading to an efficient and stereoselective synthesis of 1,1′-disaccharides, while a newly discovered 1,2-phenylseleno migration reaction in carbohydrates opened entries to 2-deoxy glycosides and orthoesters. Thus, reaction of 2-hydroxy phenylselenoglycosides with DAST led to 2-phenylselenoglycosyl fluorides which reacted with carbohydrate acceptors to afford, stereoselectively, 2-phenylselenoglycosides. The latter compounds could be reductively deselenated to 2-deoxy glycosides or oxidatively converted to orthoesters via the corresponding ketene acetals.
Details
- Title: Subtitle
- Total Synthesis of Everninomicin 13,384-1-Part 4: Explorations of Methodology; Stereocontrolled Synthesis of 1,1′-Disaccharides, 1,2-Seleno Migrations in Carbohydrates, and Solution- and Solid-Phase Synthesis of 2-Deoxy Glycosides and Orthoesters
- Creators
- K. C. Nicolaou - University of California, San DiegoKonstantina C. Fylaktakidou - University of California, San DiegoHelen J. Mitchell - University of California, San DiegoFloris L. van Delft - University of California, San DiegoRosa Maria Rodríguez - University of California, San DiegoScott R. Conley - University of California, San DiegoZhendong Jin - University of California, San Diego
- Resource Type
- Journal article
- Publication Details
- Chemistry : a European journal, Vol.6(17), pp.3166-3185
- Publisher
- WILEY-VCH Verlag
- DOI
- 10.1002/1521-3765(20000901)6:17<3166::AID-CHEM3166>3.0.CO;2-Z
- PMID
- 11002995
- ISSN
- 0947-6539
- eISSN
- 1521-3765
- Number of pages
- 20
- Language
- English
- Date published
- 09/01/2000
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984366305302771
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