Sureshan, Kana M. ; Ikeda, Kyoko ; Asano, Naoki ; Watanabe, Yutaka (2008) Efficient syntheses of optically pure chiro- and allo-inositol derivatives, azidocyclitols and aminocyclitols from myo-inositol Tetrahedron, 64 (18). pp. 4072-4080. ISSN 0040-4020
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Official URL: http://doi.org/10.1016/j.tet.2008.02.032
Related URL: http://dx.doi.org/10.1016/j.tet.2008.02.032
Abstract
Efficient routes for the syntheses of optically pure and hitherto unknown l-chiro- and d-allo-inositol derivatives, azido- and aminocyclitols of l-chiro-configuration, diazido- and diaminocyclitols of d-allo-configuration from economically viable myo-inositol are described. These routes provide access to synthetically flexible 1,2:4,5-di-O-isopropylidene-chiro-inositol and 1,6:3,4-di-O-isopropylidene-allo-inositol, which are otherwise difficult to synthesize directly from their parent inositols. A one pot methodology that allows rapid access to both chiro- and allo-inositol derivatives has also been developed. Investigations on the glycosidase inhibitory properties of these novel azido- and amino-inositols unraveled the potentials of these classes of compounds as novel class of glycosidase inhibitors. Both d and l forms of these cyclitols could be synthesized from myo-inositol in gram scales and hence by exploiting the difference in reactivities of cis- and trans-ketals, a variety of protected derivatives, which are useful for the synthesis of unnatural phosphoinositols and natural products, can be synthesized.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
ID Code: | 119867 |
Deposited On: | 17 Jun 2021 13:56 |
Last Modified: | 17 Jun 2021 13:56 |
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