Sulfonate protecting groups. synthesis of O- and C-methylated inositols: D- and L-ononitol, D- and L-laminitol, mytilitol and scyllo-inositol methyl ether
| Title | Sulfonate protecting groups. synthesis of O- and C-methylated inositols: D- and L-ononitol, D- and L-laminitol, mytilitol and scyllo-inositol methyl ether |
| Publication Type | Journal Article |
| Year of Publication | 2005 |
| Authors | Sarmah, MP, Shashidhar, MS, Sureshan, KM, Gonnade, RG, Bhadbhade, MM |
| Journal | Tetrahedron |
| Volume | 61 |
| Issue | 18 |
| Pagination | 4437-4446 |
| Date Published | MAY |
| Type of Article | Article |
| ISSN | 0040-4020 |
| Keywords | Cyclitol, Inositol, Orthoester, Protecting group, sulfonate |
| Abstract | Syntheses of D- and L-ononitol, D- and L-laminitol, mytilitol and scyllo-inositol methyl ether starting from myo-imositol are described. One or two of the inyo-inositol 1,3,5-orthoformate hydroxyl groups were protected as tosylates. These mono or ditosylates served as key intermediates for the preparation of O- and C-methyl inositols. Racemic 2,4-di-O-tosyl-myo-inositol 1,3,5-orthoformate was resolved as its diastereomeric camphanates. Use of sulfonate groups for the protection of inositol hydroxyl groups resulted in substantial improvement in the overall yield of O- and C-methyl inositols. (c) 2005 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tet.2005.02.073 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.645 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry
Physical and Materials Chemistry