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Studies on the Synthesis and Structure of New Urea‐Linked Sugar Podando‐Coronand Derivatives
Author(s) -
Charbonnier Florence,
Marsura Alain,
Roussel Kevin,
Kovács József,
Pintér István
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010321)84:3<535::aid-hlca535>3.0.co;2-t
Subject(s) - chemistry , urea , cyclam , isocyanate , phosphine , sugar , molecule , combinatorial chemistry , organic chemistry , computational chemistry , stereochemistry , polyurethane , catalysis , metal
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‐6 A ‐isocyanato‐6 A ‐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.