Synthesis of 3′-deoxy-3′-iminodiacetic acid and 3′-deoxy-3′-aminodiethanol thymidine analogues and NMR study of their complexation with boronic acids - Archive ouverte HAL
Article Dans Une Revue Tetrahedron Année : 2017

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

Résumé

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.
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hal-02197212 , version 1 (30-07-2019)

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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⟩
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