197302-88-8

Upstream product

• 632-20-2 D-Threonine 
• 108-24-7 acetic anhydride 
• 176791-97-2 (4S,5R)-1-((4R,5S)-2,5-Dimethyl-4,5-dihydro-oxazole-4-carbonyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 176791-96-1 (4S,5R)-1-((2R,3S)-1-Acetyl-3-methyl-aziridine-2-carbonyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 197232-62-5 N-[(1R,2S)-1-((4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-imidazolidine-1-carbonyl)-2-hydroxy-propyl]-acetamide 
• 176791-98-3 (4R,5S,2'R,3'S)-1,5-dimethyl-3-(2'-acetamido-3'-acetoxybutyryl)-4-phenylimidazolidin-2-one 

Downstream Products

• 632-20-2 D-Threonine 

Relevant academic research and scientific papers

Switching Lysophosphatidylserine G Protein-Coupled Receptor Agonists to Antagonists by Acylation of the Hydrophilic Serine Amine

Three human G protein-coupled receptors (GPCRs)—GPR34/LPS1, P2Y10/LPS2, and GPR174/LPS3—are activated specifically by lysophosphatidylserine (LysoPS), an endogenous hydrolysis product of a cell membrane component, phosphatidylserine (PS). LysoPS consists of-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages. We previously generated potent and selective GPCR agonists by modification of the three modules and the ester linkage. Here, we show that a novel modification of the hydrophilic serine moiety, that is, N-acylations of the serine amine, converted a GPR174 agonist to potent GPR174 antagonists. Structural exploration of the amide functionality provided access to a range of activities from agonist to partial agonist to antagonist. The present study would provide a new strategy for the development of lysophospholipid receptor antagonists.

Ring expansion of N-acetyl aziridine-2-imides to oxazoline-4-imides, useful precursors of pure β-hydroxy α-aminoacids

Optically active N-acyl aziridine 2-imides or α-carboxylates rearrange to oxazoline-4-imides or 4-carboxylates with high regio and stereo control. This ring expansion followed by mild hydrolisis allows the synthesis of enantiomerically pure β-hydroxy α-aminoacid precursors.

Synthesis of enantiomerically pure trans aziridine-2-carboxylates by diastereoselective Gabriel-Cromwell reaction

Benzyl aziridine-2-carboxylates have been obtained in high yield and selectivity by conjugate addition of ammonia to α,β-unsaturated chiral imides followed by treatment with lithium benzyloxide. A ring-expansion of the aziridine to an oxazoline allowed th