Trichoverrin B

Base Information

• Chemical Name: Trichoverrin B
• CAS No.: 76685-82-0
• Molecular Formula: C29H40O9
• Molecular Weight: 532.631
• UNII: X8Z0864KZ5
• Nikkaji Number: J1.731.982E
• Wikidata: Q105263635
• Mol file: 76685-82-0.mol

Synonyms:Trichoverrin B;X8Z0864KZ5;76685-82-0;Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 4-((2Z,4E,6S,7R)-6,7-dihydroxy-2,4-octadienoate) 15-((2E)-5-hydroxy-3-methyl-2-pentenoate), (4beta)-;UNII-X8Z0864KZ5;TRICHOTHEC-9-ENE-4,15-DIOL, 12,13-EPOXY-, 4-((2Z,4E,6S,7R)-6,7-DIHYDROXY-2,4-OCTADIENOATE) 15-((2E)-5-HYDROXY-3-METHYL-2-PENTENOATE), (4.BETA.)-

Chemical Property of Trichoverrin B

Chemical Property:

• Vapor Pressure: 4.72E-22mmHg at 25°C
• Boiling Point: 690.3°Cat760mmHg
• Flash Point: 221.9°C
• Density: 1.28g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 12
• Exact Mass: 532.26723285
• Heavy Atom Count: 38
• Complexity: 1040

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2C(CC1)(C3(C(CC(C34CO4)O2)OC(=O)C=CC=CC(C(C)O)O)C)COC(=O)C=C(C)CCO
• Isomeric SMILES: CC1=C[C@@H]2[C@](CC1)([C@]3([C@@H](C[C@H]([C@@]34CO4)O2)OC(=O)/C=C\C=C\[C@@H]([C@@H](C)O)O)C)COC(=O)/C=C(\C)/CCO

Technology Process of Trichoverrin B

There total 15 articles about Trichoverrin 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: 60.0%

C57H86O9Si3 (82521-42-4) → trichoverrin B (76685-82-0)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1021/jo00138a041

Reference yield:

15-acetylverrucarol (2533-38-2,123301-13-3) → trichoverrin B (76685-82-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH, HMPA / 1.) THF, 2.) -10 deg C

2: LiOH, H₂O / 1,2-dimethoxy-ethane

3: 1.) NaH, n-Bu₄NI / 1.) THF, 2.) room temp.

4: 60 percent / n-Bu₄NF

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; In 1,2-dimethoxyethane;

DOI:10.1021/jo00138a041

Reference yield:

verrucarol (2198-92-7) → trichoverrin B (76685-82-0)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine

2: 1.) NaH, HMPA / 1.) THF, 2.) -10 deg C

3: LiOH, H₂O / 1,2-dimethoxy-ethane

4: 1.) NaH, n-Bu₄NI / 1.) THF, 2.) room temp.

5: 60 percent / n-Bu₄NF

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; In 1,2-dimethoxyethane;

DOI:10.1021/jo00138a041

upstream raw materials:

C₅₇H₈₆O₉Si₃

15-acetylverrucarol

verrucarol

5-hydroxy-3-methyl-2-(E)-pentenoic acid

Downstream raw materials:

verrucarin A

isororidin E

roridin A

verrucarin B

Refernces