Reveromycin A

Base Information

• Chemical Name: Reveromycin A
• CAS No.: 134615-37-5
• Molecular Formula: C₃₆H₅₂O₁₁
• Molecular Weight: 660.802
• DSSTox Substance ID: DTXSID901037039
• Nikkaji Number: J1.407.738C
• Wikidata: Q58216964
• ChEMBL ID: CHEMBL332724
• Mol file: 134615-37-5.mol

Synonyms:reveromycin A

Chemical Property of Reveromycin A

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 849°Cat760mmHg
• PKA: 4.36±0.17(Predicted)
• Flash Point: 258.7°C
• PSA: 176.89000
• Density: 1.21g/cm³
• LogP: 6.13130
• Storage Temp.: −20°C
• Solubility.: DMF: soluble
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 18
• Exact Mass: 660.35096247
• Heavy Atom Count: 47
• Complexity: 1250

Purity/Quality:

>99% by HPLC ^*data from raw suppliers

Reveromycin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCC1(CCC2(CCC(C(O2)CC=C(C)C=CC(C(C)C=CC(=O)O)O)C)OC1C=CC(=CC(=O)O)C)OC(=O)CCC(=O)O
• Isomeric SMILES: CCCC[C@]1(CC[C@]2(CC[C@@H]([C@H](O2)C/C=C(\C)/C=C/[C@@H]([C@@H](C)/C=C/C(=O)O)O)C)O[C@H]1/C=C/C(=C/C(=O)O)/C)OC(=O)CCC(=O)O
• Uses: Reveromycin A, the dominant analogue of a complex of spiroketals isolated from a Streptomyces sp., is an inhibitor of the mitogenic activity of EGF. Reveromycin A is a G1 phase cell cycle inhibitor, selectively inhibiting isoleucyl-tRNA synthetase. Reveromycin A displays antiproliferative behaviour against human cell lines KB and K562, as well as potent antifungal activity. More recently it has been shown to induce apoptosis in osteoclasts thus inhibiting bone resorption. Reveromycin A is a spiroketal antibiotic inhibitor of EGF mitogenic activity. Inhibits the signal transduction of the epidermal growth factor. May be used

Technology Process of Reveromycin A

There total 46 articles about Reveromycin A 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: 94.0%

C57H102O11Si4 (757192-11-3) → Reveromycin A (134615-37-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide;

DOI:10.1021/ol048811l

Reference yield:

Succinic acid mono-[(2S,3R,6S,8R,9S)-3-butyl-8-[(2E,4E,8E)-(6S,7S)-6-(tert-butyl-dimethyl-silanyloxy)-9-carboxy-3,7-dimethyl-nona-2,4,8-trienyl]-2-((1E,3E)-4-carboxy-3-methyl-buta-1,3-dienyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl] ester (479692-43-8) → Reveromycin A (134615-37-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/ol0060634

Reference yield:

tert-Butyl-dimethyl-[2-((2R,3S)-3-methyl-6-methylene-tetrahydro-pyran-2-yl)-ethoxy]-silane (187218-75-3) → Reveromycin A (134615-37-5)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 40 percent / Eu(fod)3 / 72 h / 0 °C

2.1: BH₃*THF

2.2: 72 percent / H₂O₂; NaOH

3.1: 2,6-lutidine

4.1: H₂ / Pd(OH)2

5.1: Dess-Martin periodinane

5.2: 88 percent / K₂CO₃ / methanol

6.1: DIBALH

6.2: 98 percent / Dess-Martin periodinane

7.1: 75 percent / Sn(OTf)2; N-ethylpiperidine

8.1: 89 percent / NaBH₄ / tetrahydrofuran; H₂O

9.1: TBAF / 50 °C

10.1: imidazole

11.1: 95 percent / DCC; DMAP / CH₂Cl₂ / 3000240 Torr

12.1: 85 percent / HF*pyridine / pyridine; tetrahydrofuran

13.1: Bu₃SnH / Pd(Ph₃P)2Cl₂

13.2: TFP / Pd₂(dba)3 / 1-methyl-pyrrolidin-2-one / 60 °C

14.1: Dess-Martin periodinane

15.1: 94 percent / TBAF / dimethylformamide

With 1-ethyl-piperidine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; borane-THF; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; dicyclohexyl-carbodiimide; bis-triphenylphosphine-palladium(II) chloride; palladium dihydroxide; Eu(fod)3; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide; 1.1: hetero-Diels-Alder reaction / 5.1: Dess-Martin oxidation / 7.2: Dess-Martin oxidation / 14.2: Stille coupling / 15.1: Dess-Martin oxidation / 16.1: Wittig extention;

DOI:10.1021/ol048811l

upstream raw materials:

Succinic acid mono-[(2S,3R,6S,8R,9S)-3-butyl-8-[(2E,4E,8E)-(6S,7S)-6-(tert-butyl-dimethyl-silanyloxy)-9-carboxy-3,7-dimethyl-nona-2,4,8-trienyl]-2-((1E,3E)-4-carboxy-3-methyl-buta-1,3-dienyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl] ester

C₅₇H₁₀₂O₁₁Si₄

tert-Butyl-dimethyl-[2-((2R,3S)-3-methyl-6-methylene-tetrahydro-pyran-2-yl)-ethoxy]-silane

1-(benzyloxy)-3-methyleneheptan-2-one

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