216319-94-7

Basic information

• Product Name: (3S,6S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-benzyl-piperazine-2,5-dione
• Synonyms: (3S,6S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-benzyl-piperazine-2,5-dione
• CAS NO: 216319-94-7
• Molecular Weight: 486.611
• Mol File: 216319-94-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3S,6S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-benzyl-piperazine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,6S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-benzyl-piperazine-2,5-dione(216319-94-7)
• EPA Substance Registry System: (3S,6S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-benzyl-piperazine-2,5-dione(216319-94-7)

Safety Data

• Hazardous Substances Data: 216319-94-7(Hazardous Substances Data)

Upstream product

• 591-51-5 phenyllithium 
• 219916-54-8 (S)-N,N'-bis(p-methoxybenzyl)-3-methylene-6-isopropylpiperazine-2,5-dione 
• 205517-34-6 (3S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-piperazine-2,5-dione 
• 74124-68-8 (6S,3Z)-3-benzylidene-6-isopropyl-piperazine-2,5-dione 
• 150351-77-2 (Z,S)-1-Acetyl-3-benzylidene-6-(1-methylethyl)piperazine-2,5-dione 
• 75525-21-2 diacetyl-cyclo(L-Val-Gly) 
• 100-52-7 benzaldehyde 
• 852994-82-2 [(2S,5S)-N,N'-bis-(4-methoxybenzyl)-5-isopropyl-3,6-dioxopiperazin-2-yl]-phosphonic acid diethyl ester 
• 835596-02-6 (3S,6S)-3-Chloro-6-isopropyl-1,4-bis-(4-methoxy-benzyl)-piperazine-2,5-dione 
• 812679-17-7 (6S,3Z)-N,N'-bis-(4-methoxybenzyl)-3-benzylidene-6-isopropyl-piperazine-2,5-dione 
• 812679-15-5 (6S,3E)-3-benzylidene-6-isopropyl-1,4-bis-(4-methoxybenzyl)-piperazine-2,5-dione 
• 6921-34-2 benzylmagnesium chloride 
• 205517-36-8 (3S,6R)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-benzyl-piperazine-2,5-dione 

Downstream Products

• 35590-86-4 (3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione 
• 63-91-2 L-phenylalanine 
• 17585-69-2 L-phenylalanine hydrochloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Relevant articles and documents

Asymmetric conjugate reductions with samarium diiodide: Asymmetric synthesis of (2S,3R)- And (2S,3S)-[2-2H,3-2H]-leucine-(S)- phenylalanine dipeptides and (2S,3R)-[2-2H,3-2H]- phenylalanine methyl ester

The highly diastereoselective samarium diiodide and D2O-promoted conjugate reduction of homochiral (E)- and (Z)-benzylidene and isobutylidene diketopiperazines (E)-5,7 and (Z)-6,8 has been demonstrated. This methodology allows the asymmetric synthesis of methyl (2S,3R)-dideuteriophenylalanine 27 in ≥95% de and >98% ee, and (2S,3R)- or (2S,3S)-dideuterioleucine-(S)- phenylalanine dipeptides 37 and 38 in moderate de, 66% and 74% respectively. A mechanism is proposed to account for this process. The Royal Society of Chemistry 2005.

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.

Stereoselective conjugate addition of organocuprates to a dehydroalanine derived diketopiperazine

An asymmetric synthesis of homochiral α-amino acids has been developed which is based on the conjugate addition of organocuprates to the dehydroalanine equivalent (3S)-N,N′-bis(p-methoxybenzyl)-3-isopropyl-6-methylenepiperazine-2,5-dione 6.