Studies on the synthesis and structure of new urea-linked sugar podando-coronand derivatives

Florence Charbonnier, Alain Marsura, Kevin Roussel, J. Kovács, I. Pintér

Research output: Article

23 Citations (Scopus)

Abstract

With the aim to develop direct, simple, and efficient coupling procedures involving saccharides and cyclodextrins (CDs), the modified Staudinger method, the phosphine imide method, was chosen as a promising versatile way to reach the goals. Thus, the new cyclam derivatives 6-9 were obtained in good yields (see Scheme). In the case of β-cyclodextrin, the method also allowed the synthesis of the icosa-O-acetyl-6A-isocyanato-6A-deoxy-β-CD sugar isocyanate 11 and of symmetrical or unsymmetrical carbohydrate carbodiimides 12 and 17 under smooth conditions and in a simple way. Structural, theoretical, and experimental investigations on several urea-like cyclams revealed the fundamental role played by permanent strong H-bonds between urea functions in the conformational equilibrium of the molecules.

Original languageEnglish
Pages (from-to)535-551
Number of pages17
JournalHelvetica Chimica Acta
Volume84
Issue number3
DOIs
Publication statusPublished - 2001

Fingerprint

Cyclodextrins
carbohydrates
sugars
ureas
Urea
Sugars
phosphine
Derivatives
isocyanates
imides
Macrocyclic Lactams
synthesis
phosphines
Imides
Carbodiimides
Isocyanates
Deoxy Sugars
Carbohydrates
molecules
Molecules

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Studies on the synthesis and structure of new urea-linked sugar podando-coronand derivatives. / Charbonnier, Florence; Marsura, Alain; Roussel, Kevin; Kovács, J.; Pintér, I.

In: Helvetica Chimica Acta, Vol. 84, No. 3, 2001, p. 535-551.

Research output: Article

Charbonnier, Florence ; Marsura, Alain ; Roussel, Kevin ; Kovács, J. ; Pintér, I. / Studies on the synthesis and structure of new urea-linked sugar podando-coronand derivatives. In: Helvetica Chimica Acta. 2001 ; Vol. 84, No. 3. pp. 535-551.
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