134053-86-4

Usage

Uses

Used in Pharmaceutical Industry:
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methoxy-, (3R-cis)(9CI) is used as a potential pharmaceutical agent for its possible biological activities. Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methoxy-, (3R-cis)(9CI)'s unique structure and classification as a heterocyclic compound suggest that it may have therapeutic applications, which are yet to be fully investigated and understood.

Upstream product

• 1319113-23-9 Cbz-L-Pro-Gly(OMe)-OMe 
• 34290-72-7 tert-butyloxycarbonyl-prolyl-glycine methyl ester 
• 134023-30-6 Boc-L-Pro-Gly(OMe)-OMe 
• 61058-42-2 Z-Pro-Gly-OMe 
• 205875-03-2 2-[((S)-1-tert-Butoxycarbonyl-pyrrolidine-2-carbonyl)-amino]-malonic acid dimethyl ester 
• 205875-04-3 methyl 1,4-dioxoperhydropyrrolo[1,2-a]pyrazine-3-carboxylate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 67-56-1 methanol 
• 205875-05-4 (3S,6RS)-6-carboxy-1,3-trimethylene-2,5-piperazinedione 

Relevant academic research and scientific papers

3-Triphenylphosphonio-2,5-piperazinediones as new chiral glycine cation equivalents

3-Triphenylphosphonio-2,5-piperazinediones were effectively synthesized from homochiral valine or proline via Boc-Val-Gly-OMe, Boc-Pro-Gly-OMe or Cbz-Pro-Gly-OMe. Retention of configuration of the primary stereogenic center of the valine and proline moieties was observed. Diastereoselective nucleophilic substitution of the triphenylphosphonium group in 2,5-piperazinediones with S-, N-, P- and C-nucleophiles was observed. The configuration of the substitution products was assigned either by their hydrolysis and decarboxylation or based on the analysis of the H-C(3)-N-H coupling constants of 3-substituted-2,5- piperazinediones derived from proline. The trans-stereoselectivity was predominant in reactions of 3-triphenylphosphonio-1,6-trimethylene-2,5- piperazinediones with the nucleophiles investigated. The stereodifferentiating ability of the proline moiety is much stronger than that of the valine unit and allowed nucleophilic α-functionalization of the glycine moiety with good to excellent diastereoselectivity.

Electrogenerated chiral cationic glycine equivalents - Part 1: The 6-methoxy derivative of cyclo(L-Pro-Gly)

The cyclic N,O-acetal cyclo(L-Pro-Gly(OMe)OMe (8) has proved to be an effective chiral electrophilic glycine equivalent which is applicable in nucleophilic substitution reactions not only under Broenstedt acid catalysis but also under Lewis acid catalysis with excellent diastereoselectivities. This chiral building block can easily be obtained by electrochemical methoxylative decarboxylation of the cyclic dipeptide 6 generated from L-proline and aminomalonic diester. Thus, enantiomerically pure D-allyl glycine has been generated.

ANODIC OXIDATION OF N-ACYL AND N-ALKOXYCARBONYL DIPEPTIDE ESTERS AS A KEY STEP FOR THE FORMATION OF CHIRAL HETEROCYCLIC SYNTHETIC BUILDING BLOCKS

The anodic oxidation of N-protected dipeptide esters using chloride as a redox catalyst can be performed regioselectively at the C-terminal amino acid.With methanol as solvent, glycine as the C-terminal, and L-valine or L-proline as N-terminal amino acid methoxylation at the glycine residue takes place.Deprotection of this product leads to the (3S,6RS)-6-methoxy-2,5-piperazinedione (3) which can be applied as a chiral cationic glycine equivalent.The exchange of the methoxy group by C-nucleophiles takes place with high trans-diastereoselectivity under steric control by the substituent in 3-position.With branched amino acids at the C-terminus of the dipeptide ester the anodic oxidation in acetonitrile/methanol (95:5) as solvent with tetraethylammonium chloride as supporting electrolyte and redox catalyst leads to methyl imidazolidin-4-one-2-carboxylates.The cyclization takes place via the intermediate formation of the N-acylimino ester of the C-terminal amino acid.