76843-83-9

Upstream product

• 105933-68-4 N-benzyloxycarbonyl-α-(p-nitrobenzyl)-(Z)-α,β-dehydroglutamic-γ-O-(p-nitrobenzyl)hydroxamic acid 
• 105933-67-3 N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutamate 
• 501-53-1 benzyl chloroformate 
• 104754-70-3 erythro, threo-DL-N-benzyloxycarbonyl-α-amino-2-(p-methoxybenzyl)-3-oxo-5-isoxazolidineacetic acid o-nitrobenzyl ester 
• 104754-69-0 N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid 
• 76843-81-7 erythro-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid o-nitrobenzyl ester 
• 104754-60-1 p-nitrobenzyl-N-benzyloxycarbonyl-2-aminotetrahydro-5-oxo-2-furancarboxylate 
• 104754-62-3 N-benzyloxycarbonyl-α-(p-nitrobenzyl)-(Z)-α,β-dehydroglutamate 
• 80132-08-7 threo-DL-N-benzyloxycarbonyl-α-amino-3-oxo-5-isoxazolidineacetic acid 
• 104754-63-4 N-benzyloxycarbonyl-(Z)-α,β-dehydroglutamic-γ-hydroxamic acid 
• 80132-10-1 threo-DL-N-benzyloxycarbonyl-α-amino-3-oxo-5-isoxazolidineacetic acid diphenylmethyl ester 
• 80148-34-1 threo-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid diphenylmethyl ester 
• 104754-68-9 o-nitrobenzyl N-benzyloxycarbonyl-2-aminotetrahydro-5-oxo-2-furancarboxylate 
• 104754-51-0 N-benzyloxycarbonyl-2-aminotetrahydro-5-oxo-2-furancarboxylic acid 

Downstream Products

• 42228-92-2 erythro-DL-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid <(+/-)-AT-125> 

Relevant academic research and scientific papers

TOTAL SYNTHESIS OF ANTITUMOR AGENT AT-125, (αS,5S)-α-AMINO-3-CHLORO-4,5-DIHYDRO-5-ISOXAZOLEACETIC ACID

A short and efficient total synthesis of racemic AT-125 and its racemic threo isomer proceeds via an intramolecular Michael cyclization of a protected α,β-dehydroglutamic acid γ-hydroxamate.Separation of diastereomers and deprotection to racemic AT-125 followed by enzymatic resolution of the N-chloroacetamide with hog-kidney acylase provides the natural αS,5S isomer.