95723-21-0

Basic information

• Product Name: 1,4-dibenzyl-3-(2'-thiopyridyl)-6-(2-valerolactonyl)-2,5-piperazinedione (syn, minor diastereomer)
• Synonyms: 1,4-dibenzyl-3-(2'-thiopyridyl)-6-(2-valerolactonyl)-2,5-piperazinedione (syn, minor diastereomer)
• CAS NO: 95723-21-0
• Molecular Weight: 501.606
• Mol File: 95723-21-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,4-dibenzyl-3-(2'-thiopyridyl)-6-(2-valerolactonyl)-2,5-piperazinedione (syn, minor diastereomer)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-dibenzyl-3-(2'-thiopyridyl)-6-(2-valerolactonyl)-2,5-piperazinedione (syn, minor diastereomer)(95723-21-0)
• EPA Substance Registry System: 1,4-dibenzyl-3-(2'-thiopyridyl)-6-(2-valerolactonyl)-2,5-piperazinedione (syn, minor diastereomer)(95723-21-0)

Safety Data

• Hazardous Substances Data: 95723-21-0(Hazardous Substances Data)

Upstream product

• 71309-70-1 ((3,4-dihydro-2H-pyran-6-yl)oxy)trimethylsilane 
• 95676-11-2 1,4-dibenzyl-3,6-bis(2'-mercaptopyridyl)-2,5-piperazinedione 
• 42492-87-5 N,N'-dibenzylpiperazine-2,5-dione 
• 89291-86-1 1,4-dibenzyl-3,6-dibromopiperazine-2,5-dione 
• 100-39-0 benzyl bromide 

Relevant articles and documents

Divergent, Generalized Synthesis of Unsymmetrically Substituted 2,5-Piperasinediones

N,N'-Disubstituted 2,5-piperazinediones (12) can be 3,6-dibrominated followed by displacement with sodium 2-mercaptopyridine to furnish syn-1,4-disubstituted 3,6-bis(2'-thiopyridyl)-2,5-piperazinediones (8) in high yield.Precomplexation of these sulfides with silver(I) triflate followed by addition of trimethylsilyl enol ethers leads to chemoselective C-C bond formation, furnishing the homologated piperazinediones 10.The remaining sulfide functionality of 10 is relatively inert to a second substitution.These electrophylic 2,5-piperazinediones provide access to relatively inaccessible, unsymmetrical 2,5-piperazinediones and provide advantages over the corresponding well-known enolate anion approach.Substrates that contain N-p-methoxybenzyl residues can be deprotected to the lipophobic N,N'-unsubstituted 2,5-piperazinediones with aqueous ceric ammonium nitrate.The diastereoselectivity observed in the coupling reactions is discussed in the context of a single crystal X-ray structure determination of 20.