α-Selective Organocatalytic Synthesis of 2-Deoxygalactosides

α-Selective Organocatalytic Synthesis of 2-Deoxygalactosides

Alpha rules: A thiourea acts as an efficient organocatalyst for the glycosylation of protected galactals to form oligosaccharides containing a 2‐deoxymonosaccharide moiety (see scheme). The reaction is highly stereoselective for α‐linkages and proceeds by way of a syn‐addition mechanism.

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Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2012-09, Vol.51 (36), p.9152-9155
Hauptverfasser: Balmond, Edward I., Coe, Diane M., Galan, M. Carmen, McGarrigle, Eoghan M.
Format: Artikel
Sprache:eng
Schlagworte:
acetals
Acetals - chemistry
Catalysis
deoxyglycosides
diastereoselectivity
Galactosides - chemical synthesis
Galactosides - chemistry
Glycosylation
organocatalysis
Stereoisomerism
thiourea
Thiourea - chemistry
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Beschreibung
Zusammenfassung:Alpha rules: A thiourea acts as an efficient organocatalyst for the glycosylation of protected galactals to form oligosaccharides containing a 2‐deoxymonosaccharide moiety (see scheme). The reaction is highly stereoselective for α‐linkages and proceeds by way of a syn‐addition mechanism.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201204505