Efficient synthesis of optically active α-substituted glutamate analogs possessing α-hydroxymethyl and α-alkoxymethyl groups

M Kawasaki, K Namba, H Tsujishima, T Shinada…

Index: Kawasaki, Masanori; Namba, Kosuke; Tsujishima, Hidekazu; Shinada, Tetsuro; Ohfune, Yasufumi Tetrahedron Letters, 2003 , vol. 44, # 6 p. 1235 - 1238

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Citation Number: 21

Abstract

Highly enantioselective synthesis of (2R)-α-(hydroxymethyl) glutamate (1), a selective agonist of mGluR2 and 3, was achieved in short steps using an asymmetric version of the Strecker synthesis. This was converted into its α-methoxymethyl-and α-benzyloxymethyl derivatives 2 and 3, possible ligands as tools to investigate glutamate receptors, via protection of the sterically hindered amino group by means of phase transfer catalyst.