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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 16
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Original Articles

A Simple, General and Efficient Method for O and N-Retinoylation. Application to The Synthesis of 2-Retinoyl-Lecithin

Charles Sangmam Laboratoire de Chimie Biomoléculaire, associé au CNRS, Case 073, Université de Montpellier II, Place Eugène Bataillon, 34095, Montpellier Cédex, 05, France
,
Jean-Yves Winum Laboratoire de Chimie Biomoléculaire, associé au CNRS, Case 073, Université de Montpellier II, Place Eugène Bataillon, 34095, Montpellier Cédex, 05, France
,
Marc Lucas Laboratoire de Chimie Biomoléculaire, associé au CNRS, Case 073, Université de Montpellier II, Place Eugène Bataillon, 34095, Montpellier Cédex, 05, France
,
Jean-Louis Montero Laboratoire de Chimie Biomoléculaire, associé au CNRS, Case 073, Université de Montpellier II, Place Eugène Bataillon, 34095, Montpellier Cédex, 05, France
&
Claude Chavis Laboratoire de Chimie Biomoléculaire, associé au CNRS, Case 073, Université de Montpellier II, Place Eugène Bataillon, 34095, Montpellier Cédex, 05, France
Pages 2945-2958 | Received 11 Mar 1998, Published online: 23 Aug 2006
 
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Abstract

The synthesis of the new l-stearoyl-2-retinoyl-glycero-3-phosphorylcholine by coupling of retinoic acid and lysolecithin with DCC-DMAP (1.2 eq.) is reported. This method is applied to O and N-retinoylation of uncharged organic substrates such as aliphatic alcohols, free hydroxyl anomeric sugars, aromatic amines and C-protected α-aminoacids.

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