PM-toxin B

Base Information

• Chemical Name: PM-toxin B
• CAS No.: 87879-56-9
• Molecular Formula: C₃₃H₆₂O₈
• Molecular Weight: 586.85
• DSSTox Substance ID: DTXSID90236679
• Nikkaji Number: J1.462.783I
• Wikidata: Q27149773
• Mol file: 87879-56-9.mol

Synonyms:PM-toxin B;87879-56-9;(6R,14R,22R,30R,32S)-6,14,22,30,32-pentahydroxytritriacontane-8,16,24-trione;8,16,24-Tritriacontanetrione, 6,14,22,30,32-pentahydroxy-, (6R,14R,22R,30R,32S)-;PM toxin B;CHEBI:80725;DTXSID90236679;C33H62O8;C33-H62-O8;Q27149773

Chemical Property of PM-toxin B

Chemical Property:

• Vapor Pressure: 1.03E-26mmHg at 25°C
• Boiling Point: 760.7°Cat760mmHg
• Flash Point: 427.8°C
• PSA: 152.36000
• Density: 1.059g/cm³
• LogP: 5.51030
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 30
• Exact Mass: 586.44446893
• Heavy Atom Count: 41
• Complexity: 668

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(CC(=O)CCCCCC(CC(=O)CCCCCC(CC(=O)CCCCCC(CC(C)O)O)O)O)O
• Isomeric SMILES: CCCCC[C@H](CC(=O)CCCCC[C@H](CC(=O)CCCCC[C@H](CC(=O)CCCCC[C@H](C[C@H](C)O)O)O)O)O

Technology Process of PM-toxin B

There total 25 articles about PM-toxin B 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: 82.0%

(8R,16R,24R)-8,16,24-Trihydroxy-1-((4R,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-nonacosane-6,14,22-trione → PM-Toxin B (87879-56-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 0 ℃;

DOI:10.1039/b007617l

Reference yield: 37.6%

6,14,22-tri(benzyl)oxy-30,32-dihydroxy-8,16,24-trioxotritriacontane → (+/-)-PM-toxin B (87879-56-9)

Guidance literature:

With hydrogen; palladium; In 1,4-dioxane; water; acetic acid; 35 deg C, 24 h; 35 deg C, 24 h;

DOI:10.1080/00021369.1985.10866672

Reference yield:

methyl (+/-)-8-bromo-3-oxooctanoate (64670-06-0) → (+/-)-PM-toxin B (87879-56-9)

Guidance literature:

Multi-step reaction with 15 steps

1: NaBH₄ / methanol / 1 h / 0 °C

2: 1 M DIBAL / tetrahydrofuran; hexane / 1 h / -20 °C

3: p-TsOH / dioxane / 1 h / 20 °C

4: 1.) Mg, I₂ / 1.) THF; 2.) THF

5: pyridinium dichromate / dimethylformamide

6: BF₃*etherate / CH₂Cl₂

7: 4-dimethylaminopyridine, triethylamine / CH₂Cl₂

8: NaH, Bu₄NI / tetrahydrofuran

9: p-TsOH / methanol; CHCl₃

10: CrO₃ / pyridine

11: 1.) Mg, I₂ / 1.) THF; 2.) THF

12: CrO₃ / pyridine

13: 97.7 percent / aq. AcOH / tetrahydrofuran / 5 h / 50 °C

14: 64.9 percent / HgCl₂, HgO / acetonitrile; H₂O / 4 h / 25 °C

15: 37.6 percent / H₂ / Pd black / acetic acid; dioxane; H₂O / 35 deg C, 24 h; 35 deg C, 24 h

With chromium(VI) oxide; dmap; sodium tetrahydroborate; dipyridinium dichromate; boron trifluoride diethyl etherate; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; acetic acid; triethylamine; mercury dichloride; mercury(II) oxide; palladium; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/00021369.1985.10866672

upstream raw materials:

methyl (+/-)-8-bromo-3-oxooctanoate

8-Bromo-octane-1,3-diol

(+/-)-8-bromo-1,3-dihydroxyoctane-1,3-isopropylideneacetal

methyl (+/-)-8-bromo-3-hydroxyoctanoate