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(+)-proto-Quercitol, a natural versatile chiral building block for the synthesis of the α-glucosidase inhibitors, 5-amino-1,2,3,4-cyclohexanetetrols

✍ Scribed by Sumrit Wacharasindhu; Wisuttaya Worawalai; Wimolpun Rungprom; Preecha Phuwapraisirisan

Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 436 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.02.153

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✦ Synopsis

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 (+)-protoquercitol was addressed using the modified Mosher's method. Of the synthesized aminocyclitols, 11 potentially inhibits a-glucosidase with an IC 50 value of 12.5 lM, which is 45 times greater than that of the standard antidiabetes drug, Acarbose Ò .

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