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

✍ Scribed by Masanori Kawasaki; Kosuke Namba; Hidekazu Tsujishima; Tetsuro Shinada; Yasufumi Ohfune

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 99 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02810-1

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✦ Synopsis

Highly enantioselective synthesis of (2R)-a-(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 a-methoxymethyland a-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.

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