Tryprostatin A

Base Information

• Chemical Name: Tryprostatin A
• CAS No.: 171864-80-5
• Molecular Formula: C22H27N3O3
• Molecular Weight: 381.47
• DSSTox Substance ID: DTXSID701017629
• Nikkaji Number: J701.451A
• Wikidata: Q27140127
• Pharos Ligand ID: JMDT8CRYA8F7
• Metabolomics Workbench ID: 66102
• ChEMBL ID: CHEMBL289159
• Mol file: 171864-80-5.mol

Synonyms:tryprostatin A

Chemical Property of Tryprostatin A

Chemical Property:

• Melting Point: 119-120 °C
• Boiling Point: 666.4±55.0 °C(Predicted)
• PKA: 12.99±0.40(Predicted)
• PSA: 74.43000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 2.98380
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 381.20524173
• Heavy Atom Count: 28
• Complexity: 645

Purity/Quality:

98% ^*data from raw suppliers

TryprostatinA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCC1=C(C2=C(N1)C=C(C=C2)OC)CC3C(=O)N4CCCC4C(=O)N3)C
• Isomeric SMILES: CC(=CCC1=C(C2=C(N1)C=C(C=C2)OC)C[C@H]3C(=O)N4CCC[C@H]4C(=O)N3)C

Technology Process of Tryprostatin A

There total 66 articles about Tryprostatin A 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: 78.0%

tert-butyl 3-((S)-2-(tert-butoxycarbonylamino)-3-((S)-2-(methoxycarbonyl)pyrrolidin-1-yl)-3-oxopropyl)-6-methoxy-2-(3-methylbut-2-enyl)-indole-1-carboxylate (1261060-29-0) → Tryprostatin A (171864-80-5)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 2h; Reflux; Inert atmosphere;

DOI:10.1002/anie.201004963

Reference yield: 40.0%

(8aS)-methyl 3-((6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl)methyl)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazine-3-carboxylate → Tryprostatin A (171864-80-5) + 9-epi-tryprostatin A (171864-80-5)

Guidance literature:

With water; lithium chloride; In dimethyl sulfoxide; at 160 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.112

Reference yield: 40.0%

(8aS)-methyl 3-((6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl)methyl)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazine-3-carboxylate → Tryprostatin A (171864-80-5) + 9-epi-tryprostatin A (171864-80-5)

Guidance literature:

With water; lithium chloride; In dimethyl sulfoxide; at 160 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.112

upstream raw materials:

3-((S)-2-Ethoxycarbonyl-2-{[(S)-1-(2,2,2-trichloro-ethoxycarbonyl)-pyrrolidine-2-carbonyl]-amino}-ethyl)-6-methoxy-2-(3-methyl-but-2-enyl)-indole-1-carboxylic acid tert-butyl ester

3-{(S)-2-Ethoxycarbonyl-2-[((S)-pyrrolidine-2-carbonyl)-amino]-ethyl}-6-methoxy-2-(3-methyl-but-2-enyl)-indole-1-carboxylic acid tert-butyl ester

6-methoxy-3-methyl-1H-indole

tert-butyl 6-methoxy-3-methyl-1H-indole-1-carboxylate