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Stereospecific synthesis and absolute configuration of the (2S,3S,4S)-isomer of 2-methyl-2-(carboxycyclopropyl)glycine (MCCG)

✍ Scribed by Hassan Pajouhesh; Kenneth Curry; Hossein Pajouhesh; Mahmonir H. Meresht; Brian Patrick

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 202 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00049-1

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✦ Synopsis

The conformationally restricted metabotropic glutamate receptor antagonist (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine 1 (MCCG) has been synthesized in a stereoselective manner (>99% ee) with the (2S,3S,4S) absolute configuration of this molecule being confirmed by X-ray crystallographic analysis. Subsequent physico-chemical studies were undertaken and the data are at odds with those of the commercially available product.

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