(3R,6R)-3,6-dimethylpiperazine-2,5-dione

Base Information

• Chemical Name: (3R,6R)-3,6-dimethylpiperazine-2,5-dione
• CAS No.: 23927-13-1
• Molecular Formula: C₆H₁₀N₂O₂
• Molecular Weight: 142.158
• Hs Code.: 2933599090
• UNII: WMN9UY0GSE
• DSSTox Substance ID: DTXSID50350289
• Nikkaji Number: J1.041.401F
• Wikidata: Q82126150
• ChEMBL ID: CHEMBL4468051
• Mol file: 23927-13-1.mol

Synonyms:Cyclo(-D-Ala-D-Ala);23927-13-1;(3R,6R)-3,6-dimethylpiperazine-2,5-dione;D-Alanine anhydride;WMN9UY0GSE;Cyclo(D-alanyl-D-alanyl);2,5-Piperazinedione, 3,6-dimethyl-, (3R,6R)-;Alanine anhydride, cis-(+)-;2,5-Piperazinedione, 3,6-dimethyl-, (3R-cis)-;Cyclo(D-Ala-D-Ala);(3R,6R)-Dimethyl-piperazine-2,5-dione;starbld0009559;UNII-WMN9UY0GSE;CARBAMOYL-DL-ASPARTICACID;CHEMBL4468051;SCHEMBL13074412;DTXSID50350289;MFCD00236939;AKOS006274201;AT17302;CS-0357210

Chemical Property of (3R,6R)-3,6-dimethylpiperazine-2,5-dione

Chemical Property:

• PSA: 65.18000
• LogP: -0.43880
• Storage Temp.: -15°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 142.074227566
• Heavy Atom Count: 10
• Complexity: 159

Purity/Quality:

99%+, ^*data from raw suppliers

Cyclo(-D-Ala-D-Ala) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)NC(C(=O)N1)C
• Isomeric SMILES: C[C@@H]1C(=O)N[C@@H](C(=O)N1)C
• Uses: Cyclo(-D-Ala-D-Ala) is used in the synthetic preparation of (arylsulfenylphenyl)-substituted piperazineacetic acids as glycine transporter 1 inhibitors.

Technology Process of (3R,6R)-3,6-dimethylpiperazine-2,5-dione

There total 22 articles about (3R,6R)-3,6-dimethylpiperazine-2,5-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

Boc?D-Ala?D-Ala?OMe → (3R,6R)-3,6-dimethylpiperazine-2,5-dione (23927-13-1,5845-62-5)

Guidance literature:

Boc?D-Ala?D-Ala?OMe; With trifluoroacetic acid; In dichloromethane; at 30 ℃; for 6h;

With morpholine; In tert-butyl alcohol; at 20 ℃; for 24h;

DOI:10.1016/j.bioorg.2021.104828

Reference yield: 62.0%

(3R,6R)-1,4-Dihydroxy-3,6-dimethyl-piperazine-2,5-dione (83727-16-6) → (3R,6R)-3,6-dimethylpiperazine-2,5-dione (23927-13-1,5845-62-5)

Guidance literature:

With hydrogen; nickel; In methanol;

Reference yield:

N-[(benzyloxy)carbonyl]-L-alanyl-L-alanine methyl ester (2483-51-4) → (+/-)-cis-3,6-dimethyl-piperazine-2,5-dione (5625-46-7,5845-61-4,23927-13-1,35590-65-9,72904-45-1,5845-62-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; Yield given. Multistep reaction; 1.) methanol, 12M hydrochloric acid, 12 h, 2.) methanol 65 deg C;

upstream raw materials:

L-Alanine methyl ester

L-Alanine ethyl ester

Z-Ala-Ala-OMe

(3R,6R)-1,4-Dihydroxy-3,6-dimethyl-piperazine-2,5-dione

Downstream raw materials:

C₅₈H₆₂N₆O₈S₂

C₅₁H₅₇N₅O₈S

N,N-Bis-[4-((2S,5S)-2,5-dimethyl-piperazine-1-carbonyl)-benzyl]-4-methyl-benzenesulfonamide

(2S,5S)-2,5-Dimethyl-piperazine-1-carboxylic acid benzyl ester

Refernces

• 1、 Zhu, Long-Qing,Fan, Xiao-Hong,Li, Jun-Fang,Chen, Jin-Hong,Liang, Yan,Hu, Xiao-Ling,Ma, Shu-Meng,Hao, Xiang-Yong,Shi, Tao,Wang, Zhen. "Discovery of a novel inhibitor of nitric oxide production with potential therapeutic effect on acute inflammation". supporting information. . Retrieved 2021/05/26.
• 2、 Simon, Ga?lle,Bérubé, Christopher,Voyer, Normand,Grenier, Daniel. "Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens". . p. 2323 - 2331. Retrieved 2018/12/11.