Capped guanidino-α-cyclodextrin first synthesis based on intramolecular Staudinger-Aza-Wittig (SAW) reaction

C Couturier; F Dumarcay-Charbonnier; A Lambert; D Barth; A Marsura

doi:10.1016/j.pharma.2014.06.004

Capped guanidino-α-cyclodextrin first synthesis based on intramolecular Staudinger-Aza-Wittig (SAW) reaction

Ann Pharm Fr. 2014 Nov;72(6):422-8. doi: 10.1016/j.pharma.2014.06.004. Epub 2014 Jul 23.

Authors

C Couturier¹, F Dumarcay-Charbonnier², A Lambert², D Barth³, A Marsura⁴

Affiliations

¹ Université de Lorraine, Laboratoire Réactions et Génie des procédés, UMR CNRS 7274, 54001 Nancy, France; Université de Lorraine, Laboratoire Structure et Réactivité des Systèmes Moléculaires Complexes, UMR CNRS 7565, Nancy, France. Electronic address: [email protected].
² Université de Lorraine, Laboratoire Structure et Réactivité des Systèmes Moléculaires Complexes, UMR CNRS 7565, Nancy, France.
³ Université de Lorraine, Laboratoire Réactions et Génie des procédés, UMR CNRS 7274, 54001 Nancy, France.
⁴ Université de Lorraine, Laboratoire Structure et Réactivité des Systèmes Moléculaires Complexes, UMR CNRS 7565, Nancy, France. Electronic address: [email protected].

PMID: 25438653
DOI: 10.1016/j.pharma.2014.06.004

Abstract

An intramolecularly promoted SAW reaction between a phosphinimide and an isocyanate intermediate led to an original bridged trisubstituted ((A,C),E)-α-cyclodextrin. The latter was in a second step converted into a new capped (ACE)-(guanidino)-α-cyclodextrin.

Keywords: Réaction de Staudinger-Aza-Wittig; Staudinger-Aza-Wittig reaction; Synthesis; Synthèse; α-Cyclodextrin; α-Cyclodextrine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged-Ring Compounds / chemical synthesis
Bridged-Ring Compounds / chemistry
Carbon Dioxide / chemistry
Guanidine / chemistry*
Indicators and Reagents
Models, Molecular
alpha-Cyclodextrins / chemistry*

Substances

Bridged-Ring Compounds
Indicators and Reagents
alpha-Cyclodextrins
Carbon Dioxide
Guanidine