Synthesis of eight-membered iminocyclitols from D-glucose
| Title | Synthesis of eight-membered iminocyclitols from D-glucose |
| Publication Type | Journal Article |
| Year of Publication | 2010 |
| Authors | Jadhav, VH, Bande, OP, Puranik, VG, Dhavale, DD |
| Journal | Tetrahedron |
| Volume | 66 |
| Issue | 15 |
| Pagination | 2830-2834 |
| Date Published | APR0 |
| ISSN | 0040-4020 |
| Keywords | Baylis-Hillman reaction, Conjugate addition, diastereoselectivity, Iminosugars |
| Abstract | The Baylis-Hillman reaction of 3-o-benzyl-alpha-d-xylo-pentodialdo-1,4-furanose 2 afforded a diastereomeric mixture of L-ido- and D-gluco-configurated alpha-methylene-beta-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. (C) 2010 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tet.2010.02.044 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.011 |
Divison category:
Center for Material Characterization (CMC)