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Synthesis and Conformational Analysis of Fructose ‐ Derived Scaffolds: Molecular Diversity from a Single Molecule
Author(s) -
Cipolla Laura,
Forni Eleonora,
JiménezBarbero Jesus,
Nicotra Francesco
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020902)8:17<3976::aid-chem3976>3.0.co;2-7
Subject(s) - chemistry , molecule , stereochemistry , fructose , molecular mechanics , bicyclic molecule , tricyclic , combinatorial chemistry , organic chemistry
Bi‐ and tricyclic compounds were synthesized starting from fructose. The different hydroxyl groups present in fructose were exploited in the formation of a number of conformationally constrained sugar‐based scaffolds, including azido acids. Introduction of an azido group and carboxy terminus into different bicyclic iodo ethers, allowed the synthesis of different conformationally constrained azido acids. Conformational analysis of compounds 10, 11, 17 , and 20 by NMR experiments assisted by molecular mechanics, allowed the determination of the distances between the relevant functional groups, that is the azido and carboxy functionalities.