De Novo Asymmetric Bio- and Chemocatalytic Synthesis of Saccharides − Stereoselective Formal O-Glycoside Bond Formation Using Palladium Catalysis

De Novo Asymmetric Bio- and Chemocatalytic Synthesis of Saccharides − Stereoselective Formal O-Glycoside Bond Formation Using Palladium Catalysis

A novel integrated bio- and chemocatalytic approach to the de novo catalytic asymmetric synthesis of saccharides has been developed. Acetoxypyranones obtained enantiopure by enzymatic resolution have been shown to undergo highly stereoselective palladium-catalyzed formal O-glycoside bond formation....

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Veröffentlicht in:Journal of the American Chemical Society 2003-07, Vol.125 (29), p.8714-8715
Hauptverfasser: Comely, Alex C, Eelkema, Rienk, Minnaard, Adriaan J, Feringa, Ben L
Format: Artikel
Sprache:eng
Schlagworte:
Acetals - chemistry
Carbohydrates - chemical synthesis
Carbohydrates - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Catalysis
Chemistry
Exact sciences and technology
Glycosides - chemical synthesis
Glycosides - chemistry
Organic chemistry
Palladium - chemistry
Preparations and properties
Pyrans - chemistry
Stereoisomerism
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Beschreibung
Zusammenfassung:A novel integrated bio- and chemocatalytic approach to the de novo catalytic asymmetric synthesis of saccharides has been developed. Acetoxypyranones obtained enantiopure by enzymatic resolution have been shown to undergo highly stereoselective palladium-catalyzed formal O-glycoside bond formation. The combination of these protocols can be applied to the iterative asymmetric catalytic synthesis of saccharides.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0347538