Radical-Mediated Synthesis of α-C-Glycosides Based on N-Acyl Galactosamine

C-Glycosides of N-acyl 2-amino-2-deoxygalactose (acyl = MeCO, CF3CO, t-BuOCO) are available in a stereoselective manner by trapping of an anomeric radical with an activated alkene. Using anomeric selenides, radical generation and trapping is carried out under conditions that avoid competitive reduct...

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Bibliographic Details
Published in:Organic letters 2000-12, Vol.2 (25), p.4051-4054
Main Authors: SanMartin, Raul, Tavassoli, Bahareh, Walsh, Kenneth E, Walter, Daryl S, Gallagher, Timothy
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Benzyl Compounds - chemical synthesis
Free Radicals - chemistry
Galactosamine - analogs & derivatives
Galactosamine - chemistry
Glycosides - chemical synthesis
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Summary:C-Glycosides of N-acyl 2-amino-2-deoxygalactose (acyl = MeCO, CF3CO, t-BuOCO) are available in a stereoselective manner by trapping of an anomeric radical with an activated alkene. Using anomeric selenides, radical generation and trapping is carried out under conditions that avoid competitive reduction, and this chemistry has been applied to the synthesis of the novel C-glycoside analogue of O-benzyl α-d-GalNAc.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol006682c