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; Jean-Jacques Vasseur; Carine Baraguey; Michaël Smietana

doi:10.1016/j.tet.2017.03.033

Back

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

Journal article

Peer reviewed

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, Jean-Jacques Vasseur, Carine Baraguey and Michaël Smietana

Tetrahedron, Vol.73(17), pp.2468-2475

04/2017

DOI: https://doi.org/10.1016/j.tet.2017.03.033

Abstract

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.

Files and links (1)

url

Find in HALView

Metrics

1 Record Views

Details

Title: Synthesis of 3′-deoxy-3′-iminodiacetic acid and 3′-deoxy-3′-aminodiethanol thymidine analogues and NMR study of their complexation with boronic acids
Creators - without role: Renaud Barbeyron - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Jean-Jacques Vasseur - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Carine Baraguey - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Michaël Smietana - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Publication Details: Tetrahedron, Vol.73(17), pp.2468-2475
Identifiers: 9947913009311
Academic Unit: Institut des Biomolécules Max Mousseron - IBMM
Language: English
Resource Type: Journal article
Local Fields: hal-02197212