Synthesis of 3′-deoxy-3′-iminodiacetic acid and 3′-deoxy-3′-aminodiethanol thymidine analogues and NMR study of their complexation with boronic acids

Renaud Barbeyron (1) , Jean-Jacques Vasseur (1) , Carine Baraguey (1) , Michaël Smietana (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

The iminodiacetic acid and aminodiethanol moieties are known for their ability to generate with boronic acids bicyclic structures having a strong intramolecular N-B coordination. We describe here the convergent synthesis of 3'-deoxy-3'-iminodiacetic acid and 3'-deoxy-3'-aminodiethanol thymidine analogues. The abilities of these compounds to form boronate complexes with aliphatic or aromatic boronic acids were established by 1D and 2D H-1 and C-13 NMR. Moreover, conformational analysis of the newly synthesized compounds revealed a marked preference for an N-type sugar puckering.

Domaines: Chimie; Chimie organique; Chimie analytique

Renaud Barbeyron, Jean-Jacques Vasseur, Carine Baraguey, Michaël Smietana. Synthesis of 3′-deoxy-3′-iminodiacetic acid and 3′-deoxy-3′-aminodiethanol thymidine analogues and NMR study of their complexation with boronic acids. Tetrahedron, 2017, 73 (17), pp.2468-2475. ⟨10.1016/j.tet.2017.03.033⟩. ⟨hal-02197212⟩