A New Method for the Stereoselective Synthesis of α- and β-Glycosylamines Using the Burgess Reagent

Although glycosylamines constitute an important group of carbohydrates from the standpoint of biology and medicine, methods for their synthesis typically lack substrate generality and/or result in variable stereoselectivity, especially in complex contexts. In this communication, we report an operati...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2004-05, Vol.126 (20), p.6234-6235
Main Authors: Nicolaou, K. C, Snyder, Scott A, Nalbandian, Annie Z, Longbottom, Deborah A
Format: Article
Language:English
Subjects:
Amino Sugars - chemical synthesis
Carbohydrates - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Crystallography, X-Ray
Exact sciences and technology
Indicators and Reagents
Magnetic Resonance Spectroscopy
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:Although glycosylamines constitute an important group of carbohydrates from the standpoint of biology and medicine, methods for their synthesis typically lack substrate generality and/or result in variable stereoselectivity, especially in complex contexts. In this communication, we report an operationally simple method for the synthesis of both α- and β-glycosylamines using the Burgess reagent that overcomes many of these limitations in a bare minimum of synthetic steps.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja049293c