3-Epiaphidicolin

Base Information

• Chemical Name: 3-Epiaphidicolin
• CAS No.: 38966-21-1
• Molecular Formula: C₂₀H₃₄O₄
• Molecular Weight: 338.488
• Hs Code.: 29419090
• NSC Number: 234714
• DSSTox Substance ID: DTXSID80860563
• Wikidata: Q105182557
• ChEMBL ID: CHEMBL2006768
• Mol file: 38966-21-1.mol

Synonyms:6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol;(3-alpha,4-alpha,5-alpha,17-alpha)-3,17-Dihydroxy-4-methyl-9,15-cyclo-C,18-dinor-14,15-secoandrostane-4,17-dimethanol;3-Epiaphidicolin;CC12CCC(O)C(C)(CO)C2CCC3CC4CC13CCC4(O)CO;CHEMBL2006768;DTXSID80860563;8,11a-Methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol, tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-, [3R-(3.alpha.,4.alpha.,4a.alpha.,6a.beta.,8.beta.,9.beta.,11a.beta.,11b.beta.)]-;AKOS030242058;AS-75222;FT-0622444;4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diol;6,13-BIS(HYDROXYMETHYL)-2,6-DIMETHYLTETRACYCLO[10.3.1.0(1),(1)?.0(2),?]HEXADECANE-5,13-DIOL;8,9-dimethanol, tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-, (3R-(3.alpha., 4.alpha.,4a.alpha.,6a.beta.,8.beta.,9.beta.,11a.beta.,11b.beta.))-

Chemical Property of 3-Epiaphidicolin

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 218-220 °C
• Refractive Index: 1.586
• Boiling Point: 507.8 °C at 760 mmHg
• PKA: 14.24±0.70(Predicted)
• Flash Point: 230.4 °C
• PSA: 80.92000
• Density: 1.226 g/cm³
• LogP: 2.08580
• Storage Temp.: 2-8°C
• Solubility.: ethanol: soluble1mg/mL (stable at least a week at 4°C.)
• Water Solubility.: Soluble in DMSO or methanol. Insoluble in water. Store solutions at -20°
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 338.24570956
• Heavy Atom Count: 24
• Complexity: 524

Purity/Quality:

98%,99%, ^*data from raw suppliers

(+)-Aphidicolin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC(C(C1CCC3C24CCC(C(C3)C4)(CO)O)(C)CO)O
• Description: (+)-Aphidicolin is a natural tetracyclic diterpene first isolated from the fungus C. aphidicola and shown to have antiviral activity against herpes simplex. In eukaryotic cells, it is a cell-permeable, reversible inhibitor of DNA replication, specifically blocking the activity of DNA polymerases α, δ, and ε when used at low micromolar levels. Aphidicolin can be used, at 3 μM, to arrest cells in G1/S phase or to increase gene amplification frequency.
• Uses: (+)-Aphidicolin is a naturally occurring tetracyclic diterpene with potential antiviral and antimitotical properties. Aphidicolin is a tetracyclic diterpene antibiotic isolated from fungi, notably Cephalosporium, Nigrospora, Harziella and Phoma. Aphidicolin has antibiotic, antiviral and antimitotic properties, blocking the cell cycle at early S-phase. This property has been used to synchronise cell division and is useful as a tool in cell differentiation research. Aphidicolin is a reversible inhibitor of DNA replication by inhibiting selected DNA polymerases. Aphidicolin induces apoptosis, prolongs the half-life of DNA methyltransferase, is active against Leishmania parasites and acts synergistically with the antitumour agents, vincristine and doxorubicin. A DNA polymerase inhibitor. Blocks the cell cycle at the early S-phase

Technology Process of 3-Epiaphidicolin

There total 72 articles about 3-Epiaphidicolin 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: 90.0%

3α,18-bis-tert-butyldimethylsilyloxyaphidicolin (135404-92-1) → (+)-aphidicolin (38966-21-1,52645-92-8,52645-96-2,69926-98-3,79254-70-9)

Guidance literature:

With hydrogen fluoride; In dichloromethane; acetonitrile; at -5 ℃; for 0.333333h;

Reference yield: 70.0%

3α,18-(2,2-dimethylpropylidenedioxy)aphidicolin (135436-61-2) → (+)-aphidicolin (38966-21-1,52645-92-8,52645-96-2,69926-98-3,79254-70-9)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 60 ℃; for 36h;

Reference yield:

C23H34O4 (73697-01-5) → (+/-)-aphidicolin (38966-21-1,52645-92-8,52645-96-2,69926-98-3,79254-70-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 88 percent / zinc iodide / CHCl₃

2: 97 percent / zinc iodide / CHCl₃ / 40 °C

3: 75 percent / diisobutylaluminium hydride / toluene / 0 °C

4: 80 percent / hexamethylphosphoric acid triamide / -35 °C

5: 80 percent / lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / 23 °C

6: sodium borohydride / ethanol; tetrahydrofuran / -20 °C

7: 90 percent / 4-dimethylaminopyridine, triethylamine / CHCl₃ / 23 °C

8: 86 percent / 1,3-diiodo-5,5-dimethylhydantoin / acetone; tetrahydrofuran; H₂O / 0.5 h / -20 °C

9: hydrogen / Pd/C / 760 Torr

11: 4-dimethylaminopyridine, triethylamine / CHCl₃ / 23 °C

12: 90 percent / lithium di-tert-butylamide / various solvent(s) / -130 - -120 °C

13: 2.) acetic acid / 2.) methanol, water

With dmap; sodium tetrahydroborate; 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; hydrogen; lithium bis(trimethylsilyl)amide; diisobutylaluminium hydride; acetic acid; triethylamine; zinc(II) iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; chloroform; water; acetone; toluene;

DOI:10.1021/ja00525a055

upstream raw materials:

C₂₄H₃₆O₅

aphidicol-16-ene-3α,18-diol

<17-14C>-3α,16β,18-trihydroxyaphidicolane

19-norapidicolan-16β-ol

Downstream raw materials:

(+/-)-aphidicolin

18-Phenylthio-17-noraphidicol-2-en-16-on

(+)-aphidicolin 17-acetate

3β,17-di(p-toluenesulfonyloxy)-19-noraphidicolan-16β-ol

Refernces

• 1、 Oikawa, Hideaki,Ohashi, Satoshi,Ichihara, Akitami,Sakamura, Sadao. "Biosynthesis of diterpenoid aphidicolin: Isolation of intermediates from P-450 inhibitor treated mycelia of Phoma betae". . p. 7541 - 7554. Retrieved 2007/10/03.
• 2、 Hanson, James R.,Hitchcock, Peter B.,Manickavasagar, Revathy. "THE HYDROXYLATION OF GLOBULOL AND 7-EPIGLOBULOL BY CEPHALOSPORIUM APHIDICOLA". . p. 1023 - 1026. Retrieved 2007/10/02.