Azides in Carbohydrate Chemistry

Henning S.G. Beckmann and Valentin Wittmann Fachbereich Chemie, Universitat Konstanz, Universitatsstr. 10, D-78457 Konstanz, Germany 

Organic Azides Syntheses and Applications Edited by Stefan BrSse and Klaus Banert 2010 John Wiley Sons, Ltd. ISBN 978-0-470-51998-1 

A common way for the introdnction of azides into carbohydrates is the nucleophilic replacement of leaving groups by the azide ion. These reactions can be divided into three groups substitutions at the anomeric center leading to glycosyl azides, substitutions at primary, and substitutions at secondary carbon atoms. 

Azides can also be introduced by radical addition to glycals. The classical azidonitra-tion, developed by Lemieux et al. in 1979, is a powerful method for the preparation of 

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Santoyo-Gonzdlez F, Hernandez-Mateo F (2007) Azide-Alkyne 1,3-Dipolar Cycloadditions a Valuable Tool in Carbohydrate Chemistry. 7 133-177 Saraboji K, see Ponnuswamy MN (2006) 3 81-147... 

Click chemistry has been particularly active in various fields this year. For example, ample applications of click chemistry have been seen in carbohydrate chemistry. Various /weiido-oligosacchardies and amino acid glycoconjugates were synthesized via an intermolecular 1,3-dipolar cycloaddition reaction using easily accessible carbohydrate and amino acid derived azides and alkynes as building blocks <06JOC364>. The iterative copper(I)-catalyzed... 

F. Santoyo-Gonzalez and F. Hemandez-Mateo, Azide-alkyne 1, 3-dipolar cycloadditions A valuable tool in carbohydrate chemistry, Top. Heterocycl. Chem., 7 (2007) 133-177. 

S. Dedola, S. A. Nepogodiev, and R. A. Field, Recent applications of the Cul-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry, Org. Biomol. Chem.., 5 (2007) 1006-1017. 

The importance of reactions with complex, metal hydrides in carbohydrate chemistry is well documented by a vast number of publications that deal mainly with reduction of carbonyl groups, N- and O-acyl functions, lactones, azides, and epoxides, as well as with reactions of sulfonic esters. With rare exceptions, lithium aluminum hydride and lithium, sodium, or potassium borohydride are the... 

Click chemistry has also been applied in carbohydrate chemistry. Thus, Huisgen cyclization involving a sugar azide or alkyne has been extensively used for the preparation of a wide range of carbohydrates bearing a triazole moiety in different positions. In this volume, Santoyo Gonzalez and Herndndez-Mateo present a contribution concerning azide-alkyne 1,3-dipolar cycloadditions, mostly devoted to non-anomeric positions. 

Azide-Alkyne 1,3-Dipolar Cycloadditions a Valuable Tool in Carbohydrate Chemistry... 

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