Cyclodextrins selectively modified on both rims using an O-3-debenzylative post-functionalisation, a consequence of the Sorrento meeting

S. Guitet (1) , S.A. de Beaumais (1) , Y. Blériot (2) , B. Vauzeilles (3, 3) , Y.M. Zhang (1) , M. Ménand (1) , M. Sollogoub (1)

1 FR 2769 - Chimie Moléculaire de Paris Centre
2 OrgaSynth - Synthèse organique [E5 – IC2MP équipe 5]
3 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay

A de-O-benzylation reaction induced by I-2-Et3SiH and developed by Iadonisi et al. on mono- and disaccharides was applied to per- or polybenzylated alpha-cyclodextrins to furnish compounds deprotected at position 3 of all sugar units. This methodology allows the straightforward post-functionalisation of the secondary rim of cyclodextrins already functionalised on their primary rim.

Domaines: Catalyse; Chimie organique; Autre

S. Guitet, S.A. de Beaumais, Y. Blériot, B. Vauzeilles, Y.M. Zhang, et al.. Cyclodextrins selectively modified on both rims using an O-3-debenzylative post-functionalisation, a consequence of the Sorrento meeting. Carbohydrate Research, 2012, 356, pp.278-281. ⟨10.1016/j.carres.2011.12.002⟩. ⟨hal-00824401⟩