Skip to Main content Skip to Navigation
Theses

Synthèse et réactivité de plates-formes bis-hétérocycliques : Application à la préparation de peptidomimétiques

Abstract : The objective of this work consists in constructing new bicyclic carbohydrate based scaffolds and studying their potential functionalization for peptidomimetic design. Starting from a a,ß-unsaturated sugar-ketone, we describe a rapid access to pyrazolo-pyranoside and pyrimidino-pyranoside compounds. Firstly, we present the functionalization of the pyrazolo-pyranoside platform which under acidic condition, undergo pyranoside ring-opening generating highly functionalized optically pure pyrazoles. Secondly part, the platform SMe-pyrimidino-pyranoside was functionalized by pallado-catalyzed cross-coupling reactions (Suzuki and Stille) on the pyrimidine ring. The functionalization of the pyranose system was carried out by regioselective alkylation. Finally, we use the SMe-pyrimidino-pyranoside platform for the construction of peptidomimetics of the RGD tripeptide.
Document type :
Theses
Complete list of metadata

Cited literature [10 references]  Display  Hide  Download

https://hal.univ-lorraine.fr/tel-01748478
Contributor : Thèses Ul <>
Submitted on : Thursday, March 29, 2018 - 11:36:08 AM
Last modification on : Friday, February 26, 2021 - 3:24:03 PM
Long-term archiving on: : Friday, September 14, 2018 - 10:26:06 AM

File

SCD_T_2009_0010_SAMB.pdf
Files produced by the author(s)

Identifiers

  • HAL Id : tel-01748478, version 1

Collections

Citation

Issa Samb. Synthèse et réactivité de plates-formes bis-hétérocycliques : Application à la préparation de peptidomimétiques. Autre. Université Henri Poincaré - Nancy 1, 2009. Français. ⟨NNT : 2009NAN10010⟩. ⟨tel-01748478⟩

Share

Metrics

Record views

63

Files downloads

183