Trilobacin

Base Information

• Chemical Name: Trilobacin
• CAS No.: 140224-67-5
• Molecular Formula: C₃₇H₆₆O₇
• Molecular Weight: 622.927
• DSSTox Substance ID: DTXSID401101051
• Nikkaji Number: J776.863J
• Wikidata: Q104251531
• Metabolomics Workbench ID: 143443
• ChEMBL ID: CHEMBL68179
• Mol file: 140224-67-5.mol

Synonyms:trilobacin

Chemical Property of Trilobacin

Chemical Property:

• Boiling Point: 745.5°Cat760mmHg
• Flash Point: 220.3°C
• PSA: 105.45000
• Density: 1.054g/cm³
• LogP: 7.85790
• XLogP3: 9.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 25
• Exact Mass: 622.48085444
• Heavy Atom Count: 44
• Complexity: 801

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC(C1CCC(O1)C2CCC(O2)C(CCCCCCCCCCC(CC3=CC(OC3=O)C)O)O)O
• Isomeric SMILES: CCCCCCCCCC[C@H]([C@H]1CC[C@H](O1)[C@H]2CC[C@@H](O2)[C@@H](CCCCCCCCCC[C@H](CC3=C[C@@H](OC3=O)C)O)O)O

Technology Process of Trilobacin

There total 30 articles about Trilobacin 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: 91.0%

C37H64O7 (1242076-82-9) → trilobacin (140224-67-5)

Guidance literature:

With sodium acetate; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane; water; for 6h; Radiolysis;

DOI:10.1021/ja106116v

Reference yield:

ethyl (4E)-8-benzyloxy-4-enoctanoate (181803-05-4) → trilobacin (140224-67-5)

Guidance literature:

Multi-step reaction with 21 steps

1: AD-mix-β, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

2: 1.) aq. KOH, 2.) aq. HCl / 1.) MeOH

3: TsOH / CH₂Cl₂ / 1 h / Ambient temperature

4: imidazole / dimethylformamide / 16 h / Ambient temperature

5: H₂ / Pd/C (10percent) / methanol; propionic acid / 24 h

6: PCC, celite / CH₂Cl₂ / 2 h

7: 1.) KN(SiMe₃)2 / 1.) -78 deg C, 2 h, 2.) THF-HMPA, -78 deg C -> r.t., 16 h

8: Bu₄NF / dimethylformamide / 2 h / Ambient temperature

9: 1.) Re₂O₇, lutidine, 2.) TsOH / 1.) CH₂Cl₂, 4 h, 2.) dimethoxypropane, acetone, 1 h

10: PPH₃, DEAD / benzene / 16 h

12: CH₂Cl₂ / 1 h / -20 - 0 °C

13: TsOH / methanol; H₂O / 16 h / Ambient temperature

14: pyridine / 2 h / 100 °C

15: LiAlH₄ / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating

17: I₂, PPh₃, imidazole / CH₂Cl₂ / 1 h / Ambient temperature

18: NaHCO₃ / acetonitrile / 24 h / 45 °C

19: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h

20: H₂, Rh(PPh₃)3Cl / benzene; ethanol / 2 h / Ambient temperature

21: acetyl chloride / methanol; diethyl ether / 6 h / Heating

With pyridine; 1H-imidazole; hydrogenchloride; potassium hydroxide; Wilkinson's catalyst; lithium aluminium tetrahydride; n-butyllithium; methanesulfonamide; AD-mix-β; Celite; lutidine; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium hexamethylsilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; acetyl chloride; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; propionic acid; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1021/jo961286m

Reference yield:

(R)-5-((R)-4-Benzyloxy-1-hydroxy-butyl)-dihydro-furan-2-one (181803-09-8) → trilobacin (140224-67-5)

Guidance literature:

Multi-step reaction with 18 steps

1: imidazole / dimethylformamide / 16 h / Ambient temperature

2: H₂ / Pd/C (10percent) / methanol; propionic acid / 24 h

3: PCC, celite / CH₂Cl₂ / 2 h

4: 1.) KN(SiMe₃)2 / 1.) -78 deg C, 2 h, 2.) THF-HMPA, -78 deg C -> r.t., 16 h

5: Bu₄NF / dimethylformamide / 2 h / Ambient temperature

6: 1.) Re₂O₇, lutidine, 2.) TsOH / 1.) CH₂Cl₂, 4 h, 2.) dimethoxypropane, acetone, 1 h

7: PPH₃, DEAD / benzene / 16 h

9: CH₂Cl₂ / 1 h / -20 - 0 °C

10: TsOH / methanol; H₂O / 16 h / Ambient temperature

11: pyridine / 2 h / 100 °C

12: LiAlH₄ / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating

14: I₂, PPh₃, imidazole / CH₂Cl₂ / 1 h / Ambient temperature

15: NaHCO₃ / acetonitrile / 24 h / 45 °C

16: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h

17: H₂, Rh(PPh₃)3Cl / benzene; ethanol / 2 h / Ambient temperature

18: acetyl chloride / methanol; diethyl ether / 6 h / Heating

With pyridine; 1H-imidazole; Wilkinson's catalyst; lithium aluminium tetrahydride; n-butyllithium; Celite; lutidine; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium hexamethylsilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; acetyl chloride; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; propionic acid; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo961286m

upstream raw materials:

(E)-pentadec-4-enoic acid ethyl ester

(4R,5R)-(-)-5-Hydroxy-12-pentadecan-4-olid

ethyl (4E)-8-benzyloxy-4-enoctanoate

(cis,4R,5R,12R,13R)-5-hydroxy-12,13-isopropylidenedioxytricosa-8-en-1,4-olide