exo-Glycals: Intermediates in the Synthesis of 1,1-Disubstituted C-Glycosides

The synthesis of 1,1-disubstituted C-glycosides containing amino and ester containing moieties at what is formally the anomeric site is described. Petasis olefination of pyranosyl lactones provided exo-glycals which underwent regioselective azidoselenation and subsequent radical-mediated C-glycoside...

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Bibliographic Details
Published inSynlett no. 6; pp. 869 - 872
Main Authors Woodward, Hannah, Smith, Nichola, Gallagher, Timothy
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.04.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AZIDO-PHENYLSELENYLATION
2-AMINO-2-DEOXY SUGARS
PROTECTED GLYCALS
C-glycosides
ANALOGS
azidoselenation
DONORS
GLYCOSYLATION
Petasis olefination
SELENOGLYCOSIDES
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Summary:The synthesis of 1,1-disubstituted C-glycosides containing amino and ester containing moieties at what is formally the anomeric site is described. Petasis olefination of pyranosyl lactones provided exo-glycals which underwent regioselective azidoselenation and subsequent radical-mediated C-glycoside formation.
ISSN:0936-5214
DOI:10.1055/s-0029-1219560