942619-06-9Relevant academic research and scientific papers
Stereocontrolled synthesis of iminocyclitols with an ether bridge
Sayago, Francisco J.,Fuentes, José,Angulo, Manuel,Gasch, Consolación,ángeles Pradera
, p. 4695 - 4702 (2007)
Nor-tropane related bicyclic (6+5) iminocyclitols with an ether bridge and different substituents (hydroxymethyl, aminomethyl, and aminoethyl) on C-1 are prepared starting from a β-d-psicofuranosyl cyanide. The method involves an internal nucleophilic attack of a stabilized amide ion on a 5-mesyloxy derivative. The intermediate N-acetyl O-protected iminocyclitols present atropoisomerism due to restricted rotation of the N-CO amido bond. Conformational aspects of the prepared compounds are discussed.
