Trichostatin C

Base Information

• Chemical Name: Trichostatin C
• CAS No.: 68676-88-0
• Molecular Formula: C23H32N2O8
• Molecular Weight: 464.5088
• UNII: 8K9Y0C8YN4
• DSSTox Substance ID: DTXSID601317397
• Wikidata: Q27118157
• Metabolomics Workbench ID: 56171
• ChEMBL ID: CHEMBL3353924
• Mol file: 68676-88-0.mol

Synonyms:7-(4-(dimethylamino)phenyl)-N-(glucopyranosyloxy)-4,6-dimethyl-7-oxo-2,4-heptadienamide;trichostatin C

Chemical Property of Trichostatin C

Chemical Property:

• Melting Point: 171-173°
• Boiling Point: °Cat760mmHg
• PKA: 12.85±0.70(Predicted)
• Flash Point: °C
• PSA: 148.79000
• Density: 1.33g/cm³
• LogP: 0.31250
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 464.21586598
• Heavy Atom Count: 33
• Complexity: 717

Purity/Quality:

98% ^*data from raw suppliers

TrichostatinC ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C=C(C)C=CC(=O)NOC1C(C(C(C(O1)CO)O)O)O)C(=O)C2=CC=C(C=C2)N(C)C
• Isomeric SMILES: C[C@H](/C=C(\C)/C=C/C(=O)NO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)C(=O)C2=CC=C(C=C2)N(C)C
• Uses: Trichostatin C is the first example of a glucopyranosyl hydroxamate from nature. The conjugation may act to protect the less stable N-OH group of Trichostatin A. Trichostatin C displays antifungal, antiprotozoan and antitumour activity, albeit less potent than trichostatin A Trichostatin C is an inducer of erythroid differentiation and histone H4 acetylation level.

Technology Process of Trichostatin C

There total 30 articles about Trichostatin 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:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → trichostatin D (157479-37-3,68676-88-0)

Guidance literature:

Multi-step reaction with 6 steps

1: DIAD; PPh₃ / toluene / 0.33 h / 100 °C

2: 100 percent / H₂ / Pd(OH)2/C / ethanol / 2 h / 20 °C

3: 60 percent / 2,6-lutidine / dimethylformamide / 2 h / 20 °C

4: 100 percent / methanol / 10 h / 20 °C

5: 48 percent / 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide*HCl / tetrahydrofuran / 5.5 h / 50 °C

6: 100 percent / TFA / H₂O / 1 h / 20 °C

With 2,6-dimethylpyridine; di-isopropyl azodicarboxylate; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2004.11.004

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → 6-epi-trichostatin D (68676-88-0)

Guidance literature:

Multi-step reaction with 6 steps

1: DIAD; PPh₃ / toluene / 0.33 h / 100 °C

2: 100 percent / H₂ / Pd(OH)2/C / ethanol / 2 h / 20 °C

3: 60 percent / 2,6-lutidine / dimethylformamide / 2 h / 20 °C

4: 100 percent / methanol / 10 h / 20 °C

5: 52 percent / 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide*HCl / tetrahydrofuran / 14.5 h / 50 °C

6: 91 percent / TFA / H₂O / 0.17 h / 20 °C

With 2,6-dimethylpyridine; di-isopropyl azodicarboxylate; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2004.11.004

Reference yield:

(3aR,7aS)-2-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-isoindole-1,3-dione (833476-56-5) → trichostatin D (157479-37-3,68676-88-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / H₂ / Pd(OH)2/C / ethanol / 2 h / 20 °C

2: 60 percent / 2,6-lutidine / dimethylformamide / 2 h / 20 °C

3: 100 percent / methanol / 10 h / 20 °C

4: 48 percent / 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide*HCl / tetrahydrofuran / 5.5 h / 50 °C

5: 100 percent / TFA / H₂O / 1 h / 20 °C

With 2,6-dimethylpyridine; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2004.11.004

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

4-bromo-benzaldehyde

(+)-(R)-trichostatin acid

(E)-(4R,5R)-5-(4-Bromo-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pent-2-enal

Refernces

• 1、 Hosokawa, Seijiro,Ogura, Takashi,Togashi, Hidetaka,Tatsuta, Kuniaki. "The first total synthesis of trichostatin D". . p. 333 - 337. Retrieved 2007/10/03.