(3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione

Base Information

• Chemical Name: (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione
• CAS No.: 27483-18-7
• Molecular Formula: C₁₀H₁₆N₂O₂
• Molecular Weight: 196.249
• DSSTox Substance ID: DTXSID201159678
• Nikkaji Number: J92.064I
• Wikidata: Q105330397
• ChEMBL ID: CHEMBL460676
• Mol file: 27483-18-7.mol

Synonyms:Cyclo(D-Val-L-Pro);27483-18-7;(3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione;(3R,8aS)-3-propan-2-yl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;(3R,8AS)-3-isopropylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione;Cyclo(D-Val-L-Pro-);CHEMBL460676;DTXSID201159678;AKOS032948976;EN300-20097826;(3R,8aS)-3-(propan-2-yl)-octahydropyrrolo[1,2-a]piperazine-1,4-dione;(3R,8aS)-3-(propan-2-yl)-octahydropyrrolo[1,2-a]pyrazine-1,4-dione;(3R,8aS)-Hexahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione;Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(1-methylethyl)-, (3R-trans)-

Chemical Property of (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione

Chemical Property:

• Melting Point: 153-155℃
• PSA: 49.41000
• LogP: 0.39850
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 196.121177757
• Heavy Atom Count: 14
• Complexity: 275

Purity/Quality:

≥98% ^*data from raw suppliers

Cyclo(D-Val-L-Pro) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1C(=O)N2CCCC2C(=O)N1
• Isomeric SMILES: CC(C)[C@@H]1C(=O)N2CCC[C@H]2C(=O)N1
• General Description: Based on the provided abstract, **(3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione** (also referred to as Val-Pro diketopiperazine or cyclo(D-Val-L-Pro)) is a cyclic dipeptide formed by the condensation of D-valine and L-proline, which was synthesized enzymatically using a modified nonribosomal peptide synthetase (NRPS) system. The engineered NRPS, created via subdomain swapping, demonstrated activity in producing this diketopiperazine, highlighting its potential as a target for combinatorial biosynthesis. (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione exemplifies the feasibility of reengineering NRPS modules to generate structurally diverse nonribosomal peptides.

Technology Process of (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione

There total 9 articles about (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-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: 94.0%

(3R,8aS)-6,7,8,8a-tetrahydro-1-methoxy-3-(1-methyethyl)pyrrolo[1,2-a]pyrazin-4(3H)-one (916504-70-6) → cyclo(L)-Pro-(D)-Val (27483-18-7)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1002/hlca.200690181

Reference yield:

C10H17N2O2Pol → cyclo(L)-Pro-(D)-Val (27483-18-7)

Guidance literature:

With acetic acid; In dichloromethane; for 1h; merrefield resin

DOI:10.1016/j.chembiol.2015.04.015

Reference yield:

→ cyclo(L)-Pro-(D)-Val (27483-18-7)

Guidance literature:

With hydrogenchloride; In acetic acid; at 130 ℃; for 12h;

DOI:10.1021/ja00303a019

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

t-Boc-L-valine

(3R,8aS)-6,7,8,8a-tetrahydro-1-methoxy-3-(1-methyethyl)pyrrolo[1,2-a]pyrazin-4(3H)-one

(8aS)-6,7,8,8a-tetrahydro-1-methoxypyrrolo[1,2-a]pyrazin-4(3H)-one