1225441-89-3Relevant academic research and scientific papers
Synthesis of eight-membered iminocyclitols from d-glucose
Jadhav, Vrushali H.,Bande, Omprakash P.,Puranik, Vedavati G.,Dhavale, Dilip D.
experimental part, p. 2830 - 2834 (2010/06/14)
The Baylis-Hillman reaction of 3-O-benzyl-α-d-xylo-pentodialdo-1,4-furanose 2 afforded a diastereomeric mixture of l-ido- and d-gluco-configurated α-methylene-β-hydroxy esters 3a and 3b, respectively, in 1:1 ratio. Conjugate addition of benzyl amine on 3a gave adduct 4a as a major product while, addition of benzyl amine to 3b gave only one diastereomer 4b. Reduction of ester functionality in 4a/4b, opening of 1,2-acetonide functionality followed by reductive amino-cyclization under hydrogenation condition afforded azocanes 1c/1d in good yield.
