326890-99-7

Upstream product

• 103-71-9 phenyl isocyanate 
• 326890-98-6 (S)-4-Methylaminomethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 326890-98-6 benzyl (2S,4RS)-N-benzyloxycarbonyl-4-N-methylaminomethylpyroglutamate 
• 326890-92-0 (E)-benzyl (2S)-N-benzyloxycarbonyl-4-N-methylaminomethylenepyroglutamate 
• 134038-59-8 (S)-4-Formyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 326890-90-8 benzyl (2S,4RS)-N-benzyloxycarbonyl-4-formylpyroglutamate 
• 134174-76-8 benzyl (2S)-1-benzyloxycarbonyl-4-dimethylaminomethylenepyroglutamate 

Downstream Products

• 326891-01-4 benzyl (2S,5'S)-2-benzyloxycarbonylamino-3-(1-methyl-2,4-dioxo-3-phenylhexahydropyrimidin-5-yl)propionate 
• 326891-02-5 benzyl (2S,5'R)-2-benzyloxycarbonylamino-3-(1-methyl-2,4-dioxo-3-phenylhexahydropyrimidin-5-yl)propionate 

Relevant academic research and scientific papers

Extension of ring switching strategy to the glutamate antagonist 2-(pyrimidin-2,4-dione-5-ylmethyl)-(2S)-glycine and related compounds with two chiral centres

2-(Pyrimidin-2,4-dione-5-ylmethyl)-(2S)-glycine 8 has been prepared by treatment of the pyroglutamate urea 12 with mild base, followed by deprotection in a modification of our ring switching approach to the synthesis of glutamate antagonists. The product is an isomer of the natural product willardiine 7. Use of this two step strategy has allowed us to synthesise L-alanine derivatives, which are β-substituted by a reduced pyrimidinedione containing a second chiral centre. There is little difference between the diastereoisomers of one of these compounds as antagonists at metabotropic glutamate receptors. (C) 2000 Elsevier Science Ltd.

Use of a modified ring-switching strategy to synthesise the glutamate antagonist (2s)-2-amino-3-(2,4- oxo-1,2,3,4-tetra-hydropyrimidin-5-yl)propionate and related compounds with two chiral centres

(2S)-2-Amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propionic acid8, an isomer of the natural product willardiine7, was synthesised by treatment of the pyroglutamate urea 19 with mild base followed by deprotection in a two-step modification of our 'ring-switching' approach to the synthesis of glutamate antagonists. Use of this two-step strategy has allowed us to synthesise L-alanine derivatives, which are β-substituted by a reduced pyrimidinedione which contains a second chiral centre. In one case, the antagonist activity at metabotropic glutamate receptors of two diastereoisomers showed little difference.