Synthesis of unnatural 2- and 3-deoxyfuranose analogues.

Bénédicte Dayde (1) , Claire Pierra (2) , Gilles Gosselin (2, 3) , Dominique Surleraux (2) , Amadou Tidjani Ilagouma (4) , Arie van Der Lee (5) , Jean-Noël Null Volle (1) , David Virieux (1) , Jean-Luc Pirat (1)

1 ICGM ICMMM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
2 Idenix Pharmaceuticals
3 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
4 Departement de Chimie
5 IEM - Institut Européen des membranes

This Letter describes the synthesis of two racemic analogues of unnatural 3′-deoxy and 2′-deoxy sugars, where a phosphorus atom replaces the carbon atom in the 2′- or 3′-position. Two methods of four- and 5-steps were developed affording these new unnatural sugar analogues.

Mots clés: Deoxysugar analogues; Oxaphospholane; Pudovik reaction; P-alkylation reaction

Domaines: Chimie organique

Bénédicte Dayde, Claire Pierra, Gilles Gosselin, Dominique Surleraux, Amadou Tidjani Ilagouma, et al.. Synthesis of unnatural 2- and 3-deoxyfuranose analogues.. Tetrahedron Letters, 2014, 55 (27), pp.3706-3708. ⟨10.1016/j.tetlet.2014.05.011⟩. ⟨hal-01061679⟩