Synthesis of eight-membered iminocyclitols from d-glucose |
| |
Authors: | Vrushali H. Jadhav Vedavati G. Puranik |
| |
Affiliation: | a Garware Research Centre, Department of Chemistry, University of Pune, Pune 411 007, India b Center for Materials Characterization, National Chemical Laboratory, Pune 411 008, India |
| |
Abstract: | 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. |
| |
Keywords: | Baylis-Hillman reaction Conjugate addition Iminosugars Diastereoselectivity |
本文献已被 ScienceDirect 等数据库收录! |
|