A facile synthesis of 6-deoxydapagliflozin

Autor: Yongheng Shi, Bingni Liu, Li-Da Tang, Weiren Xu, Kong Weiling, Wei Qunchao, Guilong Zhao, Hua-Qiang Xu
Rok vydání: 2013
Předmět:
Zdroj: Monatshefte für Chemie - Chemical Monthly. 144:1903-1910
ISSN: 1434-4475
0026-9247
DOI: 10.1007/s00706-013-1053-0
Popis: A facile synthesis of a potent SGLT2 inhibitor, 6-deoxydapagliflozin, from methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-d-glucopyranoside in six steps with an overall yield of 50 % is described. The key steps were the reductive deiodination of the starting iodide under hydrogenolytic conditions to build the desired 6-deoxyglucose functionality, the coupling of 2,3,4-tri-O-benzyl-6-deoxy-d-gluconolactone and (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methane, followed by BF3·Et2O-mediated reduction with Et3SiH in order to construct the desired anomeric β-configuration. A variety of methods used for the cleavage of benzyl groups in 2,3,4-tri-O-benzyl-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-1,6-dideoxy-β-d-glucopyranose were intensively screened, leading to the discovery of AlCl3-mediated cleavage as the optimal method. .
Databáze: OpenAIRE
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