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.

 

Trifluoromethylation of Electron-Rich Alkenyl Iodides with Fluoroform-Derived "Ligandless" CuCF3

J. Mestre, A. Lishchynsky, S. Castillón, O. Boutureira
J. Org. Chem. 2018, 83, 8150-8160.

We herein present a flexible approach for the incorporation of CF3 units into a predefined site of electron-rich alkenes that exploits the regiocontrolled introduction of an iodine handle and subsequent trifluoromethylation of the C(sp2)–I bond using fluoroform-derived “ligandless” CuCF3. The broad substrate scope and functional group tolerance together with the scalability and purity of the resulting products enabled the controlled, late-stage synthesis of single regioisomers of complex CF3-scaffolds, such as sugars, nucleosides (antivirals), and heterocycles (indoles and chromones), with potential for academic and industrial applications.

   

Fluorinated triazole-containing sphingosine analogues.

Syntheses and in vitro evaluation as SPHK inhibitors

M. Escudero-Casao, A. Cardona, R. Beltrán-Debón, Y. Díaz, M. Isabel Matheu, S. Castillón
Org. Biomol. Chem. 2018, 16, 7230-7235.

Sphingosine analogues with a rigid triazole moiety in the aliphatic chain and systematic modifications in the polar head and different degrees of fluorination at the terminus of the alkylic chain were synthesized from a common alkynyl aziridine key synthon. This key synthon was obtained by enantioselective organocatalyzed aziridination and it was subsequently ring opened in a regioselective manner in acidic medium. Up to 16 sphingosine analogues were prepared in a straightforward manner. The in vitro activity of the obtained products as SPHK1 and SPHK2 inhibitors was evaluated, displaying comparable activity to that of DMS.

   

Highly reactive 2-deoxy-2-iodo-D-allo and D-gulo pyranosyl sulfoxide donors

ensure b-stereoselective glycosylations with steroidal algycones

J. Mestre, D. Collado, D. Benito-Alifonso, M.A. Rodriguez, M.I. Matheu, Y. Díaz, S. Castillón, O. Boutureira.
RSC Adv. 2018, 8, 30076-30079.

The preparation of well-defined D-xylo and D-ribo glycosides represents a synthetic challenge due to the limited configurational availability of starting materials and the laborious synthesis of homogeneous 2-deoxy-β-glycosidic linkages, in particular that of the sugar-steroid motif, which represents the “stereoselective determining step” of the overall synthesis. Herein we describe the use of 2-deoxy-2-iodo-glycopyranosyl sulfoxides accessible from widely available D-xylose and D-ribose monosaccharides as privileged glycosyl donors that permit activation at very low temperature. This ensures a precise kinetic control for a complete 1,2-trans stereoselective glycosylation of particularly challenging steroidal aglycones.

   

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