Welcome to SINTCARB! 

Our group aim to provide new answers to some classical problems in connection with the synthesis of oligosaccharides and glycosides and intend also to provide efficient methods for the synthesis of sphingosines, glycosphingolipids and glycoclusters, and tackle a biologically oriented research. In this sense the SINTCARB group has a broad experience in carbohydrate chemistry and also in transition metal catalyzed reactions and asymmetric catalysis.

 

Enantioselective Synthesis of Aminodiols by Sequential Rh-Catalysed Oxyamination/Kinetic Resolution.

Expanding the Substrate Scope of Amidine-Based Catalysis

J. Guasch,. I. Giménez-Nueno, I. Funes-Ardoiz, M. Bernús, M. I. Matheu, F. Maseras, S. Castillón, Y. Díaz
Chem. Eur. J. 2018, 24, 4635-4642.

Regio- and stereoselective oxyamination of dienes through a tandem rhodium catalysed aziridination-nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process using ABCs (amidine-based catalysts) achieving s values up to 117. This protocol was applied to the enantioselective synthesis of sphingosine

   

“Chemical Access to D-Sarmentose Units Enables the Total Synthesis of Cardenolide Monoglycoside N-1

 from Nerium oleander"      
 J. Mestre, M.I. Matheu, Y. Díaz, S. Castillón, O. Boutureira
J. Org. Chem.
2017, 82, 3327-3333

Herein we present a chemical approach for the ready preparation of d-sarmentosyl donors enabling the first total synthesis and structure validation of cardenolide N-1, a challenging 2,6-dideoxy-3-O-methyl-β-d-xylo-hexopyranoside extracted from Nerium oleander twigs that displays anti-inflammatory properties and cell growth inhibitory activity against tumor cells. The strategy highlights the synthetic value of the sequential methodology developed in our group for the synthesis of 2-deoxyglycosides. Key steps include Wittig–Horner olefination of a d-xylofuranose precursor, [I+]-induced 6-endo cyclization, and 1,2-trans stereoselective glycosylation.

   

Topological Defects in Hyperbranched Glycopolymers Enhance Binding to Lectins

Míriam Salvadó, José J. Reina, Javier Rojo, Sergio Castillón, Omar Boutureira
Chemistry a European Journal, 2017, 23, 15790-15794

Central scaffold topology and carbohydrate density are important features in determining both the binding mechanism and potency of synthetic multivalent, polydisperse vs. monodisperse carbohydrate systems to a model plant toxin (RCA120). We found lower densities of protein receptors favour the use of heterogeneous, polydisperse glycoconjugate presentations as determined by surface plasmon resonance (SPR) and dynamic light scattering (DLS).

   

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