80185-83-7

Upstream product

• 80132-10-1 threo-DL-N-benzyloxycarbonyl-α-amino-3-oxo-5-isoxazolidineacetic acid diphenylmethyl ester 
• 621-84-1 O-benzyl carbamate 
• 80132-00-9 ((3R,4S)-4-Chloro-2,6-dioxo-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 
• 80131-98-2 (2R,3S)-2-Benzyloxycarbonylamino-3-chloro-pentanedioic acid 
• 80132-09-8 (S)-Benzyloxycarbonylamino-((R)-3-oxo-isoxazolidin-5-yl)-acetic acid 
• 80132-13-4 (2R,3S)-2-Benzyloxycarbonylamino-3-chloro-4-hydroxycarbamoyl-butyric acid; compound with dicyclohexyl-amine 
• 13593-90-3 L-erythro-β-chloroglutamic acid 
• 56-86-0 L-glutamic acid 
• 80132-11-2 (S)-Benzyloxycarbonylamino-((R)-3-oxo-isoxazolidin-5-yl)-acetic acid benzhydryl ester 
• 105933-68-4 N-benzyloxycarbonyl-α-(p-nitrobenzyl)-(Z)-α,β-dehydroglutamic-γ-O-(p-nitrobenzyl)hydroxamic acid 
• 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 

Downstream Products

• 76843-83-9 threo-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid 

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.