Cyclomarin A

Base Information

• Chemical Name: Cyclomarin A
• CAS No.: 169062-92-4
• Molecular Formula: C₅₆H₈₂N₈O₁₁
• Molecular Weight: 1043.31
• DSSTox Substance ID: DTXSID601347033
• Nikkaji Number: J1.236.383D
• Wikidata: Q105301903
• Metabolomics Workbench ID: 99115
• Mol file: 169062-92-4.mol

Synonyms:cyclomarin A

Chemical Property of Cyclomarin A

Chemical Property:

• XLogP3: 5.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 15
• Exact Mass: 1042.61030546
• Heavy Atom Count: 75
• Complexity: 2020

Purity/Quality:

99% ^*data from raw suppliers

CYCLOMARIN A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N1)CC(C)CO)C)C(C2=CN(C3=CC=CC=C32)C(C)(C)C4CO4)O)C(C)C=C(C)C)CC(C)C)C)C(C)C)C(C5=CC=CC=C5)OC
• Isomeric SMILES: C[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N1)C[C@@H](C)CO)C)[C@@H](C2=CN(C3=CC=CC=C32)C(C)(C)[C@@H]4CO4)O)[C@H](C)C=C(C)C)CC(C)C)C)C(C)C)[C@@H](C5=CC=CC=C5)OC

Technology Process of Cyclomarin A

There total 4 articles about Cyclomarin 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:

C62H96N8O11Si → cyclomarin A (169062-92-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/acs.orglett.5b03292

Reference yield:

C72H116N8O14Si2 → cyclomarin A (169062-92-4)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium diacetate; trisodium tris(3-sulfophenyl)phosphine; diethylamine / aq. phosphate buffer; acetonitrile / 0.5 h / 20 °C / pH 6.4

2: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dichloromethane / 18 h / 20 °C

3: ammonium fluoride / methanol / 18 h / 40 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

With ammonium fluoride; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; diethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; aq. phosphate buffer; dichloromethane; acetonitrile;

DOI:10.1021/acs.orglett.5b03292

Reference yield:

C68H112N8O12Si2 → cyclomarin A (169062-92-4)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dichloromethane / 18 h / 20 °C

2: ammonium fluoride / methanol / 18 h / 40 °C

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

With ammonium fluoride; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/acs.orglett.5b03292

Refernces

• 1、 Barbie, Philipp,Kazmaier, Uli. "Total synthesis of cyclomarins A, C and D, marine cyclic peptides with interesting anti-tuberculosis and anti-malaria activities". . p. 6036 - 6054. Retrieved 2016/07/06.