amphidinolide C

Base Information

• Chemical Name: amphidinolide C
• CAS No.: 112945-21-8
• Deprecated CAS: 111870-67-8
• Molecular Formula: C₄₁H₆₂O₁₀
• Molecular Weight: 714.937
• Wikidata: Q110184788
• Mol file: 112945-21-8.mol

Synonyms:amphidinolide C

Chemical Property of amphidinolide C

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 882.7°Cat760mmHg
• Flash Point: 261.2°C
• Density: 1.16g/cm³
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 714.43429817
• Heavy Atom Count: 51
• Complexity: 1330

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(=C)C(C(=CC=CC1C2CCC(O2)CC(=O)CC(C(=O)CC(C(C(=CC(=C)C(C(C3CC(C(O3)CC(=O)O1)C)O)O)C)C)O)C)C)O
• Isomeric SMILES: CCCCC(=C)[C@@H](/C(=C/C=C/[C@@H]1[C@H]2CC[C@@H](O2)CC(=O)C[C@@H](C(=O)C[C@@H]([C@@H](/C(=C/C(=C)[C@H]([C@H]([C@H]3C[C@H]([C@@H](O3)CC(=O)O1)C)O)O)/C)C)O)C)/C)O

Technology Process of amphidinolide C

There total 45 articles about amphidinolide C 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: 66.0%

C65H118O10Si4 → amphidinolide C (112945-21-8)

Guidance literature:

With triethylamine tris(hydrogen fluoride); triethylamine; In acetonitrile; at 40 ℃; for 96h; Schlenk technique;

DOI:10.1002/chem.201405790

Reference yield: 42.0%

C65H118O10Si4 → amphidinolide C (112945-21-8)

Guidance literature:

With triethylamine hydrofluoride; triethylamine; In acetonitrile; at 20 ℃; for 144h;

DOI:10.1021/ja404796n

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → amphidinolide C (112945-21-8)

Guidance literature:

Multi-step reaction with 21 steps

1.1: sodium nitrite; hydrogenchloride / water / 72.67 h / 0 - 20 °C

1.2: 0.16 h / 0 - 20 °C

2.1: pyridine / water / 14 h

3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: 4 h / -78 - -30 °C

3.3: 0.33 h / -78 °C

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

5.1: toluene / 16 h / 80 °C

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

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

8.1: N-ethyl-N,N-diisopropylamine; dimethyl sulfoxide; sulfur trioxide pyridine complex / dichloromethane / 1 h / 0 °C / Schlenk technique

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

10.1: pyridine / dichloromethane; ethanol / 0 - 20 °C / Schlenk technique

10.2: 0.5 h

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

11.2: 3 h / -78 °C / Schlenk technique

12.1: lithium chloride; trifuran-2-yl-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / tetrahydrofuran / 4.25 h / Schlenk technique

13.1: potassium hydroxide / tetrahydrofuran; water; ethanol / 5 h / 45 °C

14.1: triethylamine / toluene / 1 h / 20 °C / Schlenk technique; Inert atmosphere

15.1: dmap / toluene / 3 h / 20 °C / Schlenk technique

16.1: Tetrabutylammoniumsalz der Diphenylphosphinsaeure; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) thiophene-2-carboxylate / N,N-dimethyl-formamide / 1 h / 20 °C / Schlenk technique

17.1: Mo(N[((t)Bu)(3,5-C₆H₃Me₂)])3 / dichloromethane; toluene / 7.67 h / 60 °C / Schlenk technique

18.1: pyridinium p-toluenesulfonate / dichloromethane; methanol / 24 h / 0 °C / Schlenk technique

19.1: Zeise's dimer / diethyl ether / 0.25 h / 20 °C

20.1: pyridinium p-toluenesulfonate / benzene / 0.25 h / 20 °C

20.2: 2 h / 0 - 20 °C / Schlenk technique

21.1: triethylamine tris(hydrogen fluoride); triethylamine / acetonitrile / 96 h / 40 °C / Schlenk technique

With pyridine; hydrogenchloride; dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; copper(I) thiophene-2-carboxylate; trifuran-2-yl-phosphane; Zeise's dimer; Mo(N[((t)Bu)(3,5-C₆H₃Me₂)])3; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine tris(hydrogen fluoride); triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; Tetrabutylammoniumsalz der Diphenylphosphinsaeure; trifluoroacetic acid; L-proline; lithium chloride; potassium hydroxide; sodium nitrite; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 16.1: |Stille Cross Coupling;

DOI:10.1002/chem.201405790

upstream raw materials:

1,2-epoxy-5-hexene

D-Glutamic acid

hex-1-yne

C₂₀H₃₈O₂Si₂