Preparation of complex aminoglycosides: a new strategy

Aminoglycosides are widely distributed in nature and are found in a large variety of biologically important molecules. A few examples of these are aminopolysaccharides, such as blood group determinants and antigenic determinants on cell surfaces, aminoglycoside antibiotics glycoproteins, glycolipids...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1988-07, Vol.110 (15), p.5229-5231
Main Authors: Fitzsimmons, Brian J, Leblanc, Yves, Chan, Nicolas, Rokach, Joshua
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:Aminoglycosides are widely distributed in nature and are found in a large variety of biologically important molecules. A few examples of these are aminopolysaccharides, such as blood group determinants and antigenic determinants on cell surfaces, aminoglycoside antibiotics glycoproteins, glycolipids, and nucleoside antibiotics (i.e., tunicamycin). In the past, synthesis of these molecules has generally required two separate strategies, one for the preparation of the appropriate aminosugar and another for the glycosidation of this sugar. Recently, the authors have described a new mild, highly stereoselective and efficient method for the preparation of aminosugars which involve the cycloaddition of an azodicarboxylate onto a glycal. Herein, the authors report that the cycloadducts obtained by this reaction are powerful and versatile glycosylating agents and can be used to prepare a variety of complex glycosides. This allows both the aminosugar and the glycoside preparation to be combined in a single, mild, simple, and efficient strategy for the first time.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00223a073