Sarmah, Manash P. ; Shashidhar, Mysore S. ; Sureshan, Kana M. ; Gonnade, Rajesh G. ; Bhadbhade, Mohan M. (2005) Sulfonate protecting groups. Synthesis of O- and C-methylated inositols: d- and l-ononitol, d- and l-laminitol, mytilitol and scyllo-inositol methyl ether Tetrahedron, 61 (18). pp. 4437-4446. ISSN 0040-4020
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Official URL: http://doi.org/10.1016/j.tet.2005.02.073
Related URL: http://dx.doi.org/10.1016/j.tet.2005.02.073
Abstract
Syntheses of d- and l-ononitol, d- and l-laminitol, mytilitol and scyllo-inositol methyl ether starting from myo-inositol are described. One or two of the myo-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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 119860 |
| Deposited On: | 17 Jun 2021 13:02 |
| Last Modified: | 17 Jun 2021 13:02 |
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