219916-58-2

Basic information

• Product Name: (3S,6S)-N,N'-bis(4-methoxybenzyl)-3-isopropyl-6-ethylpiperazine-2,5-dione
• Synonyms: (3S,6S)-N,N'-bis(4-methoxybenzyl)-3-isopropyl-6-ethylpiperazine-2,5-dione
• CAS NO: 219916-58-2
• Molecular Weight: 424.54
• Mol File: 219916-58-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (3S,6S)-N,N'-bis(4-methoxybenzyl)-3-isopropyl-6-ethylpiperazine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,6S)-N,N'-bis(4-methoxybenzyl)-3-isopropyl-6-ethylpiperazine-2,5-dione(219916-58-2)
• EPA Substance Registry System: (3S,6S)-N,N'-bis(4-methoxybenzyl)-3-isopropyl-6-ethylpiperazine-2,5-dione(219916-58-2)

Safety Data

• Hazardous Substances Data: 219916-58-2(Hazardous Substances Data)

Upstream product

• 917-54-4 methyllithium 
• 219916-54-8 (S)-N,N'-bis(p-methoxybenzyl)-3-methylene-6-isopropylpiperazine-2,5-dione 
• 16944-60-8 (2S)-isopropylpiperazine-3,6-dione 
• 824-94-2 p-methoxybenzyl chloride 
• 205517-34-6 (3S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-piperazine-2,5-dione 
• 75-03-6 ethyl iodide 

Downstream Products

• 407578-43-2 (3S,6S)-3-isopropyl-6-ethylpiperazine-2,5-dione 

Relevant articles and documents

Conjugate additions of organocuprates to a 3-methylene-6-isopropyldiketopiperazine acceptor for the asymmetric synthesis of homochiral α-amino acids

Addition of a range of organocuprates to (S)-N,N′-bis(p-methoxybenzyl)-3-methylene-6-isopropylpiperazine-2, 5-dione 8 affords cis-3-isopropyl-6-alkyldiketopiperazines in excellent yield and >95% de. Subsequent deprotection and hydrolysis of these cis-3-isopropyl-6-alkyldiketopiperazines affords homochiral (S)-α-amino acids in excellent yield.

Chiral relay auxiliary for the synthesis of enantiomerically pure α-amino acids

Chiral auxiliary (3S)-N,N′-bis(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione employs a chiral relay network based on non-stereogenic N-benzyl protecting groups to enhance diastereocontrol during enolate alkylation.