Carbohydrate chemistry, cycloaddition

Giuliano R. M. Cycloaddition Reactions in Carbohydrate Chemistry. An Overview... 

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. 

D. Horton, D. Koh, Y. Tskagi, and T. Usui, Diels-Alder cydoaddMons to onaaturated sugars, Cycloadditions in Carbohydrate Chemistry, ACS Symp. Set 494 66 (1992). 

J. C. Lopez and G. Lukacs, Pyranose-derived dienes and conjugated enals—preparation and Diels-Alder cycloaddition reactions, in Cycloaddition Reactions in Carbohydrate Chemistry, 1992, pp. 33-49. 

Another annellation reaction starts from a,a -dibromo-o-xylene, an activated olefin and zinc.63 This reaction, according to the authors proceeds by a Diels-Alder cycloaddition via the o-xylylene (Scheme 15.10), and was employed in carbohydrate chemistry to prepare anthracyclinones analogues.64 No reaction occurs without sonication. Instead of a cycloaddition, another explanation can be postulated, consisting first of addition of a mono-organozinc reagent to the activated olefin, followed by alkylation of the resulting enolate by the second benzylic bromide. 

Celine Cano-Soumillac was born in Angouleme, France, in 1977. She studied Organic Chemistry at the University of Poitiers, France. In 1999, she went to Paris as a predoctoral fellow and worked on asymmetric synthesis of substituted piperazines from phenylglycinol derivatives, under the supervision of Prof. H.-P. Husson. In 2000, she moved back to Poitiers, where she worked on the synthesis of biomolecules by 1,3-dipolar cycloadditions with carbohydrates and received her Ph.D. degree in 2004. She then joined the group of Prof John A. Joule at the University of Manchester, UK as a postdoctoral fellow and worked on the synthesis of analogues of cofactors of oxomolybdoenzymes. She now holds a research associate position in the Northern Institute for Cancer Research, at Newcastle University, UK, where she works on the synthesis of inhibitors of DNA-dependent protein kinase. Her research interests include heterocyclic chemistry, carbohydrates chemistry, asymmetric synthesis, and development of new synthetic methodologies. 

Cycloadditions are widely used methods for carbocycle construction [352], In this context, the Diels-Alder reaction has been studied in carbohydrate chemistry. Using this approach, the sugar can be used as the dienophile or as the diene with a large preference for the former. 

For a review, see Giuliano, RM, Cycloaddition reactions in carbohydrate chemistry — an overview. In Cycloaddition Reactions in Carbohydrate Chemistry, Giuliano, RM, Ed., American Chemical Society, Washington, DC, pp. 1-23, 1992. 

Giuliano, R. M. Cycloaddition reactions in carbohydrate chemistry. An overview. ACS Symp. Ser. 1992,494,1-23. 

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. 

ChmielewskiM, KaluZaZ, Grodner J, Urbanski R (1992) In Giuliano RM (ed) Cycloaddition Reaction in Carbohydrate Chemistry. ACS Symposium Series 494 50... 

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

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