802919-85-3Relevant academic research and scientific papers
Efficient syntheses of optically pure chiro- and allo-inositol derivatives, azidocyclitols and aminocyclitols from myo-inositol
Sureshan, Kana M.,Ikeda, Kyoko,Asano, Naoki,Watanabe, Yutaka
, p. 4072 - 4080 (2008)
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.
Efficient routes to optically active azido-, amino-, di-azido- and di-amino-cyclitols with chiro- and allo-configuration from myo-inositol
Sureshan, Kana M.,Ikeda, Kyoko,Asano, Naoki,Watanabe, Yutaka
, p. 8367 - 8370 (2007/10/03)
Efficient routes to hitherto unknown 1d-2,5-di-azido-di-deoxy-allo- inositol, 1d-2,5-di-amino-di-deoxy-allo-inositol, 1l-1-azido-1-deoxy-chiro- inositol and 1l-1-amino-1-deoxy-chiro-inositol were developed by using cheaply available myo-inositol as the st
