16679-70-2

Basic information

• Product Name: (3S,6S)-3-benzyl-6-isobutylpiperazine-2,5-dione
• CAS NO: 16679-70-2
• Molecular Weight: 260.336
• Mol File: 16679-70-2.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (3S,6S)-3-benzyl-6-isobutylpiperazine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,6S)-3-benzyl-6-isobutylpiperazine-2,5-dione(16679-70-2)
• EPA Substance Registry System: (3S,6S)-3-benzyl-6-isobutylpiperazine-2,5-dione(16679-70-2)

Safety Data

• Hazardous Substances Data: 16679-70-2(Hazardous Substances Data)

Upstream product

• 38155-45-2 methyl L-phenylalanyl-L-leucinate hydrochloride 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 2666-93-5 (S)-Leu-OMe 
• 35661-40-6 N-Fmoc L-Phe 
• 3063-05-6 Leu-Phe-OH 
• 64152-76-7 methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-4-methylpentanoate 
• 2743-60-4 L-Leucine ethyl ester 
• 1416817-77-0 C₁₇H₂₃N₃O₃ 
• 6461-07-0 methyl (S)-2-[(S)-2-amino-4-methylpentanamido]-3-phenylpropanoate hydrochloride 
• 3081-24-1 H-Phe-OEt 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 15136-32-0 (N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester 
• 2953-42-6 Z-phenylalanylleucine ethyl ester 

Downstream Products

• 74124-69-9 (3Z,6S)-3-benzylidene-6-isobutylpiperazine-2,5-dione 
• 1222-90-8 (3Z,6Z)-3-benzylidene-6-(2-methylpropenyl)piperazine-2,5-dione 

Relevant articles and documents

Unified enantioselective total synthesis of 3,6-dioxygenated diketopiperazine natural products, diatretol and lepistamides A, B and C

The concise enantioselective total synthesis of Diatretol (1) has been achieved via 9 steps with 30％ yield. The synthetic approach involves stereoselective oxidation and regioselective transacetalization utilizing a folded conformation induced by an intramolecular CH/π interaction. In addition, we have also achieved total synthesis of three diketopiperazine natural products, Lepistamides A (2), B (3) and C (4).

Immobilized Carbodiimide Assisted Flow Combinatorial Protocol to Facilitate Amide Coupling and Lactamization

Through a screen of over one hundred and 30 permutations of reaction temperatures, solvents, carbodiimide resins, and carbodiimide molar equivalences, in the presence, absence, or combination of diisopropylamine and benzotriazole additives, a convenient and first reported carbodiimide polymer-assisted flow approach to effect amide coupling and lactamization was developed. The protocol entails injecting a single solution (1:9 dimethylformamide: dichloromethane) containing a carboxylic acid and an amine or linear peptide sequence into a continuous stream of dichloromethane. The protocol remained viable in the absence of base, did not require carboxylate preactivation which, and in concert with minimal workup requirements, enabled the isolation of products in high yields. Compared to the utilization of untethered carbodiimide reagents, the flow procedure was also observed to provide a degree of racemization safety.

Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides

We synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.