92098-01-6

Upstream product

• 51425-66-2 (4,5-dihydro-2-furanyloxy)(trimethyl)silane 
• 95676-11-2 1,4-dibenzyl-3,6-bis(2'-mercaptopyridyl)-2,5-piperazinedione 
• 92216-23-4 1,4-dimethyl-3-(2'-thiopyridyl)-6-(2''-δ-valerolactonyl)-2,5-piperazinedione (syn, minor diastereomer) 
• 100-39-0 benzyl bromide 
• 89291-86-1 1,4-dibenzyl-3,6-dibromopiperazine-2,5-dione 
• 42492-87-5 N,N'-dibenzylpiperazine-2,5-dione 

Downstream Products

• 92098-02-7 1,4-dibenzyl-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione 
• 92098-09-4 N,N-dibenzyl-2',3'-O-isopropylidene-bicyclomycin 
• 95694-57-8 1,4-dibenzyl-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione 
• 95694-58-9 1,4-dibenzyl-3-(2'-thiopyridyl)-6-<1''-<((tert-butyldimethylsilyl)oxy)methyl>-3''-(hydroxypropyl)>-2,5-piperazinedione 
• 92098-07-2 8,10-dibenzyl-8,10-diaza-1-methyl-5-<((tert-butyldimethylsilyl)oxy)methyl>-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 95782-40-4 8,10-dibenzyl-8,10-diaza-5-<(methylsulfonyl)methyl>-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 92098-06-1 8,10-dibenzyl-8,10-diaza-5-<((tert-butyldimethylsilyl)oxy)methyl>-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 92098-05-0 8,10-dibenzyl-8,10-diaza-5-<(phenylselenyl)methyl>-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 92216-24-5 8,10-dibenzyl-8,10-diaza-5-(hydroxymethyl)-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 95782-39-1 8,10-dibenzyl-8,10-diaza-5-(hydroxymethyl)-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 92125-40-1 8,10-dibenzyl-8,10-diaza-1-<1'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylidene>-5-<((tert-butyldimethylsilyl)oxy)methyl>-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 95739-42-7 8,10-dibenzyl-8,10-diaza-1-<1'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylidene>-5-<((tert-butyldimethylsilyl)oxy)methyl>-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 92125-39-8 8,10-dibenzyl-8,10-diaza-1-<1'-hydroxy-2',3'-O-isopropylidene>-5-<((tert-butyldimethylsilyl)oxy)methyl>-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 95694-59-0 1,4-dibenzyl-3-(2'-thiopyridyl)-6-<1''-<((tert-butyldiphenylsilyl)oxy)methyl>-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione 

Relevant academic research and scientific papers

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.