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
• General Description: Aphidicolin is a tetracyclic diterpene compound with a complex structure featuring a bicyclo[3.2.1]octane ring system and a C16,C17 diol moiety. It is known for its role as a reversible inhibitor of DNA polymerase, particularly in eukaryotic cells, and has been studied for its potential antiviral and antitumor properties. The successful total synthesis of (+)-aphidicolin demonstrates its structural complexity, involving key steps such as hetero-Diels-Alder condensation and Claisen rearrangement to achieve the correct stereochemistry and functional group placement. APHIDICOLIN's confirmed spectral and physical properties align with those of naturally derived aphidicolin, underscoring the validity of the synthetic approach.

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:

17,18-diacetoxyaphidicol-3α,16β-diol

3α,18;16β,17-bisisopropylidenedioxyaphidicolane

3α,18-isopropylidenedioxyaphidicolane-16β,17-diol

16β,17-isopropylidenedioxyaphidicolane-3α,18-diol

Refernces

Total Synthesis of (+/-)-Aphidicolin and (+/-)-β-Chamigrene

10.1021/jo00180a010

The research focuses on the total synthesis of (+)-aphidicolin and (+)-β-chamigrene, which are complex organic compounds belonging to the tetracyclic diterpene class. The purpose of the study was to develop an efficient synthetic process for these compounds, utilizing a series of chemical reactions including hetero-Diels-Alder condensation, Claisen rearrangement, and solvolytic α-route for the formation of the bicyclo[3.2.1]octane portion of the molecule. The synthesis involved a variety of chemicals such as α-methylene ketones, methyl methacrylate, quinoline, and various ester and ketone derivatives. The conclusions of the research highlighted the successful synthesis of the target compounds, with a particular focus on the rearrangement of intermediates to form the aphidicolane bicyclo[3.2.1]octane ring system, which was a central feature of the (+)-aphidicolin synthesis. The study also detailed the challenges encountered in the synthesis process, such as the introduction of the C16,C17 diol system and the stereochemical control of the hydroxylation of exo-olefinic ketone. The final product, (+)-aphidicolin, was confirmed to have the same physical and spectral properties as an authentic sample, validating the synthetic route developed in the study.