Sureshan, Kana M. ; Watanabe, Yutaka (2004) An efficient route to optically active inositol derivatives via the resolution of myo-inositol 1,3,5-orthoformate: a short synthesis of d-myo-inositol-4-phosphate Tetrahedron: Asymmetry, 15 (7). pp. 1193-1198. ISSN 0957-4166
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Official URL: http://doi.org/10.1016/j.tetasy.2004.02.020
Related URL: http://dx.doi.org/10.1016/j.tetasy.2004.02.020
Abstract
An efficient method for the resolution of myo-inositol 1,3,5-orthoformate has been developed. The triol, 1 was converted to diastereomers via reaction with (S)-O-acetylmandeloyl chloride. Conditions were optimized for a diastereomeric ratio of 7:3. Both the diastereomers could be separated by column chromatography. The absolute configurations of the diastereomers were determined by converting the less polar diastereomer to the known l-2,4-di-O-benzyl-myo-inositol. The utility of the resolved derivatives is illustrated by a short and efficient synthesis of d-myo-inositol-4-phosphate in four steps from myo-inositol.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 119811 |
| Deposited On: | 17 Jun 2021 08:15 |
| Last Modified: | 17 Jun 2021 08:15 |
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