[reaction: see text] The construction of multivalent neoglycoconjugates is efficiently achieved by the regiospecific catalytic cycloaddition of alkynes and azides using the organic-soluble copper complexes (Ph(3)P)(3).CuBr and (EtO)(3)P.CuI. The simultaneous use of microwave irradiation shortened notably the reaction times.
The construction of multivalent structures such as sugar heterodimers, glycoclusters, calix sugars, multicalixarenes, and glycocyclodextrins is designed by using 1,3-dipolar cycloaddition as a versatile and efficient tool which allows the creation of heterocyclic bridges between the different units that are coupled.
Carbohydrates
Carbohydrates U 0500Multivalent Neoglycoconjugates by Regiospecific Cycloaddition of Alkynes and Azides Using Organic-Soluble Copper Catalysts. -The construction of multivalent neoglycoconjugates is efficiently achieved using a regiospecific catalytic cycloaddition of carbohydrate-derived alkynes (I) and azides (II) in the presence of soluble copper complexes CuBr (PPh3)3 or CuI·P(O-Et)3. Use of polyazides like (IV) or cyclic polyazidoglycosides then provides access to multivalent neoglycoconjugates. Reaction times can be significantly shortened by the use of microwave irradiation. -(PEREZ-BALDERAS, F.; ORTEGA-MUNOZ, M.; MORALES-SANFRUTOS, J.; HERNANDEZ-MATEO, F.; CALVO-FLORES, F. G.; CALVO-ASIN, J. A.; ISAC-GARCIA, J.; SANTOYO
N -Pivaloyl imidazole was prepared and used as a selective protective reagent of different monosaccharides (D-glucose, D-mannose, D-galactose, 2-acetamido-2-deoxy-D-glucose and 2acetamido-2-deoxy-β -D-glucopyranosyl azide) and lactose. A variety of pivalates were obtained with moderate or good regioselectivity.
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