Publication: (+)-proto-Quercitol, a natural versatile chiral building block for the synthesis of the α-glucosidase inhibitors, 5-amino-1,2,3,4-cyclohexanetetrols
Issued Date
2009-05-13
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ISSN
00404039
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2-s2.0-62949090610
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Mahidol University
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SCOPUS
Bibliographic Citation
Tetrahedron Letters. Vol.50, No.19 (2009), 2189-2192
Suggested Citation
Sumrit Wacharasindhu, Wisuttaya Worawalai, Wimolpun Rungprom, Preecha Phuwapraisirisan (+)-proto-Quercitol, a natural versatile chiral building block for the synthesis of the α-glucosidase inhibitors, 5-amino-1,2,3,4-cyclohexanetetrols. Tetrahedron Letters. Vol.50, No.19 (2009), 2189-2192. doi:10.1016/j.tetlet.2009.02.153 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/27229
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Title
(+)-proto-Quercitol, a natural versatile chiral building block for the synthesis of the α-glucosidase inhibitors, 5-amino-1,2,3,4-cyclohexanetetrols
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Abstract
An efficient synthesis of diastereomerically pure 5-amino-1,2,3,4-cyclohexanetetrols (6 and 11) and quercitol derivatives from naturally available (+)-proto-quercitol (1) is described. The stereochemistry of 1 is perfectly set up for regioselective protection of the hydroxy group which was further functionalized into the target aminocyclitol in a straightforward manner. The present approach provides a protocol for preparing aminocyclitols in large quantities. In addition, the absolute stereochemistry of (+)-proto-quercitol was addressed using the modified Mosher's method. Of the synthesized aminocyclitols, 11 potentially inhibits α-glucosidase with an IC50value of 12.5 μM, which is 45 times greater than that of the standard antidiabetes drug, Acarbose®. © 2009 Elsevier Ltd. All rights reserved.