Amphidinolide F

Base Information

• Chemical Name: Amphidinolide F
• CAS No.: 139594-87-9
• Molecular Formula: C₃₅H₅₂O₉
• Molecular Weight: 616.792
• Nikkaji Number: J454.144H
• Metabolomics Workbench ID: 171465
• Mol file: 139594-87-9.mol

Synonyms:amphidinolide F

Chemical Property of Amphidinolide F

Chemical Property:

• Vapor Pressure: 2.56E-30mmHg at 25°C
• Boiling Point: 809.3°Cat760mmHg
• Flash Point: 249.3°C
• PSA: 139.59000
• Density: 1.17g/cm³
• LogP: 4.33140
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 616.36113323
• Heavy Atom Count: 44
• Complexity: 1130

Purity/Quality:

95%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C(C(C(=C)C=C(C(C(CC(=O)C(CC(=O)CC3CCC(O3)C(OC(=O)CC1O2)C=CC=C(C)C)C)O)C)C)O)O
• Isomeric SMILES: CC1CC2C(C(C(=C)/C=C(/C(C(CC(=O)C(CC(=O)CC3CCC(O3)C(OC(=O)CC1O2)/C=C/C=C(C)C)C)O)C)\C)O)O

Technology Process of Amphidinolide F

There total 157 articles about Amphidinolide F 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: 60.0%

C53H94O9Si3 → amphidinolide F (139594-87-9)

Guidance literature:

With triethylamine tris(hydrogen fluoride); triethylamine; In acetonitrile; at 40 ℃; for 72h; Schlenk technique;

DOI:10.1002/anie.201301700

Reference yield: 56.0%

C53H94O9Si3 → amphidinolide F (139594-87-9)

Guidance literature:

With triethylamine hydrofluoride; triethylamine; In acetonitrile; at 20 ℃; for 168h;

DOI:10.1021/ja404796n

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → amphidinolide F (139594-87-9)

Guidance literature:

Multi-step reaction with 20 steps

1.1: pyridine / 0.14 h

2.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

2.2: 4 h / -30 °C

2.3: 0.75 h / -78 - 0 °C

3.1: diisobutylaluminium hydride / hexane; dichloromethane / 1.5 h / -78 °C

4.1: ethyl (triphenylphosphoranylidene)acetate / toluene / 16 h / 80 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C

6.1: trifluoroacetic acid / dichloromethane; ethanol / 1 h / 0 °C

7.1: N-ethyl-N,N-diisopropylamine; dimethyl sulfoxide / benzene; dichloromethane / 0.01 h / 0 °C / Schlenk technique

7.2: 1 h / 0 °C / Schlenk technique

8.1: L-proline / N,N-dimethyl-formamide / 18 h

9.1: pyridine / dichloromethane / 20 °C

9.2: 0.5 h

10.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C / Schlenk technique

10.2: 3 h / -78 °C / Inert atmosphere

11.1: lithium chloride; trifuran-2-yl-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / tetrahydrofuran / 3.25 h

12.1: potassium hydroxide; water / tetrahydrofuran; ethanol / 5 h / 45 °C / Inert atmosphere

13.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 1 h / Schlenk technique

13.2: 3 h / Schlenk technique

14.1: Tetrabutylammoniumsalz der Diphenylphosphinsaeure; copper(I) thiophene-2-carboxylate; triphenylphosphine / N,N-dimethyl-formamide / 2 h / 20 °C / Schlenk technique

15.1: pyridinium p-toluenesulfonate / dichloromethane; methanol / 0 °C

16.1: molybdenum catalyst / toluene / 100 °C

17.1: Zeise's dimer / diethyl ether / 0.33 h / 20 °C / Schlenk technique

18.1: pyridinium p-toluenesulfonate / benzene / 0.33 h / 20 °C

19.1: tetra-n-propylammonium perruthenate. / dichloromethane / 2 h / 20 °C

20.1: triethylamine tris(hydrogen fluoride); triethylamine / acetonitrile / 72 h / 40 °C / Schlenk technique

With pyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; tetra-n-propylammonium perruthenate.; copper(I) thiophene-2-carboxylate; trifuran-2-yl-phosphane; Zeise's dimer; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine tris(hydrogen fluoride); triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; Tetrabutylammoniumsalz der Diphenylphosphinsaeure; trifluoroacetic acid; ethyl (triphenylphosphoranylidene)acetate; L-proline; lithium chloride; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1002/anie.201301700

upstream raw materials:

C₃₂H₅₄O₇Si₂

C₂₅H₅₀O₆Si₂

C₂₆H₅₀O₆Si₂

C₂₆H₅₂O₆Si₂

Refernces

• 1、 Valot, Galle,Mailhol, Damien,Regens, Christopher S.,O'Malley, Daniel P.,Godineau, Edouard,Takikawa, Hiroshi,Philipps, Petra,Fürstner, Alois. "Concise total syntheses of amphidinolides C and F". supporting information. p. 2398 - 2408. Retrieved 2015/02/05.
• 2、 Mahapatra, Subham,Carter, Rich G.. "Exploiting hidden symmetry in natural products: Total syntheses of amphidinolides C and F". . p. 10792 - 10803. Retrieved 2013/08/23.