Stereoselective synthesis of (2S)-2-hydroxymethylglutamic acid, a potent agonist of metabotropic glutamate receptor mGluR3
โ Scribed by Prabir K Choudhury; Bao Khanh Le Nguyen; Nicole Langlois
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 54 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Straightforward stereocontrolled synthesis of (2S)-2-hydroxymethylglutamic acid was achieved from (S)-pyroglutaminol, through a bicyclic silyloxypyrrole derived from the versatile unsaturated lactam 3.
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AbstractรThe ยฎrst synthesis of one of the 4 possible stereoisomers of 3,4-dihydroxy-l-glutamic acid ((3S,4S)-DHGA 3), a natural product of unknown conยฎguration, is described. The synthesis is based on the Lewis acid catalyzed reaction of benzyl alcohol with a d-ribose-derived 2,3-aziridino-g-lactone