Curacin A

Base Information

• Chemical Name: Curacin A
• CAS No.: 155233-30-0
• Molecular Formula: C₂₃H₃₅NOS
• Molecular Weight: 373.603
• UNII: S9C9YBJ48Q
• ChEMBL ID: CHEMBL89138
• DSSTox Substance ID: DTXSID001032406
• Metabolomics Workbench ID: 70501
• NCI Thesaurus Code: C1676,C1678
• Wikidata: Q25323731
• Wikipedia: Curacin_A
• Mol file: 155233-30-0.mol

Synonyms:curacin A;curacin B;curacin C

Chemical Property of Curacin A

Chemical Property:

• Vapor Pressure: 1.29E-08mmHg at 25°C
• Boiling Point: 471.7°Cat760mmHg
• PKA: 4.39±0.40(Predicted)
• Flash Point: 239.1°C
• PSA: 46.89000
• Density: 1.01g/cm³
• LogP: 5.80210
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 12
• Exact Mass: 373.24393591
• Heavy Atom Count: 26
• Complexity: 561

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: other linear non-peptide
• Canonical SMILES: CC1CC1C2=NC(CS2)C=CCCC=CC=C(C)CCC(CC=C)OC
• Isomeric SMILES: C[C@H]1C[C@H]1C2=N[C@@H](CS2)/C=C\CC/C=C/C=C(\C)/CC[C@H](CC=C)OC

Technology Process of Curacin A

There total 98 articles about Curacin 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: 63.0%

(1R,2S)-2-methylcyclopropanecarbothioic acid [(1R,2Z,6E,8E,12R)-1-(hydroxymethyl)-12-methoxy-9-methylpentadeca-2,6,8,14-tetraenyl]amide (174971-56-3) → curacin A (155233-30-0)

Guidance literature:

With Et₃NSO₂NCO₂CH₂CH₂OPEG; In tetrahydrofuran; at 21 ℃; for 1h;

DOI:10.1021/jo960845m

Reference yield: 50.0%

(1R,2S)-2-Methyl-cyclopropanecarbothioic acid ((2Z,6E,8E)-(1R,12R)-1-hydroxymethyl-12-methoxy-9-methyl-pentadeca-2,6,8,14-tetraenyl)-amide → curacin A (155233-30-0) + curacin B

Guidance literature:

With Burgess Reagent; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/0040-4039(95)02337-2

Reference yield:

cis-2-methylcyclopropanecarboxylic acid (29667-48-9) → curacin A (155233-30-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / pyBOP; Et₃N / CH₂Cl₂ / 0 - 20 °C

2: 58 percent / P₄S₁₀; Na₂CO₃ / tetrahydrofuran / 17 h / 0 - 20 °C

3: NaNO₂; aq. AcOH / 0.5 h / 0 °C

4: 379 mg / dimethylformamide / 2 h / 0 °C

5: 50 percent / Burgess' reagent / tetrahydrofuran / 2 h

With tetraphosphorus decasulfide; Burgess Reagent; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium carbonate; acetic acid; triethylamine; sodium nitrite; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b206796j

upstream raw materials:

(3Z,7E,9E)-(2R,13R)-2-Amino-13-methoxy-10-methyl-hexadeca-3,7,9,15-tetraene-1-thiol

(1R,2S)-2-Methyl-cyclopropanecarbothioic acid S-((3Z,7E,9E)-(2R,13R)-2-tert-butoxycarbonylamino-13-methoxy-10-methyl-hexadeca-3,7,9,15-tetraenyl) ester

(4E,6E)-(R)-10-Methoxy-7-methyl-trideca-4,6,12-trienal

(1R,2S)-2-methylcyclopropanecarbothioic acid [(1R,2Z,6E,8E,12R)-1-(hydroxymethyl)-12-methoxy-9-methylpentadeca-2,6,8,14-tetraenyl]amide