Phorbol-13,20-diacetate

Base Information

• Chemical Name: Phorbol-13,20-diacetate
• CAS No.: 41621-85-6
• Molecular Formula: C24H32 O8
• Molecular Weight: 448.513
• European Community (EC) Number: 636-999-0
• Mol file: 41621-85-6.mol

Synonyms:phorbol 13,20-diacetate

Chemical Property of Phorbol-13,20-diacetate

Chemical Property:

• Vapor Pressure: 4.92E-16mmHg at 25°C
• Boiling Point: 583.3°C at 760 mmHg
• Flash Point: 194.4°C
• PSA: 130.36000
• Density: 1.34g/cm³
• LogP: 1.07170
• Storage Temp.: ?20°C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 448.20971797
• Heavy Atom Count: 32
• Complexity: 963

Purity/Quality:

98%Min ^*data from raw suppliers

PHORBOL-13,20-DIACETATE 98.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 26/27/28-36/37/38
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C2(C(C2(C)C)C3C1(C4C=C(C(=O)C4(CC(=C3)COC(=O)C)O)C)O)OC(=O)C)O

Technology Process of Phorbol-13,20-diacetate

There total 22 articles about Phorbol-13,20-diacetate 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: 89.0%

phorbol (17673-25-5) + acetic anhydride (108-24-7) → Phorbol 13,20-diacetate (41621-85-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; dichloromethane; for 8h;

DOI:10.1055/s-1999-3656

Reference yield:

C27H40O8Si → Phorbol 13,20-diacetate (41621-85-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;

DOI:10.1038/nature17153

Reference yield:

C33H57F3O8Si3 → Phorbol 13,20-diacetate (41621-85-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: dmap / dichloromethane / 0 °C

2.1: triethylamine / N,N-dimethyl-formamide / 60 °C

3.1: methanol / Reflux

4.1: acetic acid; sodium cyanoborohydride / methanol / Reflux

5.1: chromium(VI) oxide; 3,5-dimethyl-1H-pyrazole / dichloromethane / 0 - 20 °C

6.1: trimethylsilylazide / 1,2-dichloro-ethane / 70 °C

6.2: 70 °C

7.1: bis(benzonitrile)palladium(II) dichloride; triphenyl-arsane; copper(l) iodide / 1-methyl-pyrrolidin-2-one / 80 °C

8.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 °C

9.1: Martins sulfurane / 1,2-dichloro-ethane / 60 °C

10.1: selenium(IV) oxide / benzene / 80 °C

11.1: sodium tetrahydroborate / methanol / -40 °C

12.1: dmap / dichloromethane

13.1: sodium tris(acetoxy)borohydride / benzene / Reflux

14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; dmap; selenium(IV) oxide; sodium tetrahydroborate; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; Martins sulfurane; triphenyl-arsane; trimethylsilylazide; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; sodium cyanoborohydride; pyridine hydrogenfluoride; acetic acid; triethylamine; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene; 7.1: |Stille Cross Coupling;

DOI:10.1038/nature17153

upstream raw materials:

phorbol

acetic anhydride

(1aR,1bR,2R,3R,7bR,8R,9aR)-2-((tert-butyldimethylsilyl)oxy)-1,1,3,8-tetramethyl-7b-((trimethylsilyl)oxy)-1,1a,1b,2,3,5,7b,8,9,9a-decahydro-6H-cyclopropa[3,4]benzo[1,2-e]azulen-6-one

Downstream raw materials:

12-O-dodecanoylphorbol-13-acetate

12-O-n-Hexanoyl-phorbol-13-acetat

12-O-n-Octanoyl-phorbol-13-acetat

phorbol 12-Myristate