Synthesis of gamma-aminobutyric acid analogs based on carbohydrate scaffolds.
Gamma-aminobutyric acid analogs based on sugar scaffolds were prepared in six to nine steps starting from D-glucal and D-galactal. The key step in the synthesis is the Vilsmeier-Haack reaction that affords the corresponding 2-C-formyl glycal on treatment with DMF and POCl(3). Oxidation of the aldehyde and reduction of the 4-azido group provided the corresponding GABA analog. Acylamide and tetrazole analogs were also prepared as the bioisosteres of the carboxylic acid.
Zhong
Ming
M
National Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Science, Peking University, Beijing, China.
Meng
Xiang-Bao
XB
Li
Zhong-Jun
ZJ
D002241:Carbohydrates / Q000737:chemistry*; D013237:Stereoisomerism; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D002241:Carbohydrates; D005680:gamma-Aminobutyric Acid