Orevactaene

Base Information

• Chemical Name: Orevactaene
• CAS No.: 197631-20-2
• Molecular Formula: C₃₄H₄₄O₁₀
• Molecular Weight: 612.717
• Wikidata: Q105006931
• ChEMBL ID: CHEMBL310705
• Mol file: 197631-20-2.mol

Synonyms:orevactaene

Chemical Property of Orevactaene

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 910.1°C at 760 mmHg
• Flash Point: 286.5°C
• PSA: 0.00000
• Density: 1.28g/cm³
• LogP: 0.00000
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 15
• Exact Mass: 612.29344760
• Heavy Atom Count: 44
• Complexity: 1280

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C)CC(C)C=C(C=C(C)C=CC=CC=CC=CC=CC1=CC2=C(C(C(C(O2)C(C(CO)O)O)O)O)C(=O)O1)C(=O)O
• Isomeric SMILES: CCC(C)CC(C)/C=C(/C=C(\C)/C=C/C=C/C=C/C=C/C=C/C1=CC2=C([C@@H]([C@H]([C@@H](O2)C(C(CO)O)O)O)O)C(=O)O1)\C(=O)O

Technology Process of Orevactaene

There total 16 articles about Orevactaene 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: 17.0%

C68H124O10Si6 → epipyrone A (197631-20-2)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Darkness; Inert atmosphere;

DOI:10.1002/anie.201702189

Reference yield:

(2S,4S)-2,4-dimethylhexanal (42330-30-3) → epipyrone A (197631-20-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

1.2: 2.75 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - 20 °C / Inert atmosphere

2.2: 18 h / -78 - 20 °C / Inert atmosphere

3.1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

3.2: 0.17 h / -78 °C / Inert atmosphere

4.1: trimethylamine-N-oxide; potassium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water / 1.5 h / 70 °C / Inert atmosphere

5.1: copper(l) cyanide / tetrahydrofuran / 0.67 h / -50 - -10 °C / Inert atmosphere

5.2: 0.5 h / -50 - -10 °C / Inert atmosphere

5.3: 2 h / -50 - -10 °C / Inert atmosphere

6.1: Dess-Martin periodane / dichloromethane / 1.5 h / Inert atmosphere

7.1: sodium dihydrogenphosphate; dihydrogen peroxide / water; tert-butyl alcohol / 0.08 h / 0 °C / Inert atmosphere

7.2: 16 h / 0 °C / Inert atmosphere

8.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 2.25 h / 0 - 20 °C / Inert atmosphere

9.1: N-iodo-succinimide; 2,6-dimethylpyridine / 0.03 h / 0 °C / Inert atmosphere

10.1: dichloro bis(acetonitrile) palladium(II); triphenyl-arsane; Tetrabutylammoniumsalz der Diphenylphosphinsaeure / N,N-dimethyl-formamide / 20 h / 20 °C / Darkness; Inert atmosphere; Schlenk technique

10.2: 0.08 h / Inert atmosphere; Darkness; Schlenk technique

10.3: 18 h / Inert atmosphere; Schlenk technique; Darkness

11.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / N,N-dimethyl-formamide / 16 h / 20 °C / Darkness; Inert atmosphere

With 2,6-dimethylpyridine; dichloro bis(acetonitrile) palladium(II); (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium dihydrogenphosphate; N-iodo-succinimide; n-butyllithium; trimethylamine-N-oxide; triphenyl-arsane; tris(dimethylamino)sulfonium trimethylsilyldifluoride; dihydrogen peroxide; copper(l) cyanide; Dess-Martin periodane; triphenylphosphine; Tetrabutylammoniumsalz der Diphenylphosphinsaeure; potassium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: |Corey-Fuchs Alkyne Synthesis / 2.1: |Corey-Fuchs Alkyne Synthesis / 2.2: |Corey-Fuchs Alkyne Synthesis;

DOI:10.1002/anie.201702189

Reference yield:

(3S,5S)-1,1-dibromo-3,5-dimethyl-1-heptene (446262-65-3) → epipyrone A (197631-20-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - 20 °C / Inert atmosphere

1.2: 18 h / -78 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

2.2: 0.17 h / -78 °C / Inert atmosphere

3.1: trimethylamine-N-oxide; potassium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water / 1.5 h / 70 °C / Inert atmosphere

4.1: copper(l) cyanide / tetrahydrofuran / 0.67 h / -50 - -10 °C / Inert atmosphere

4.2: 0.5 h / -50 - -10 °C / Inert atmosphere

4.3: 2 h / -50 - -10 °C / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 1.5 h / Inert atmosphere

6.1: sodium dihydrogenphosphate; dihydrogen peroxide / water; tert-butyl alcohol / 0.08 h / 0 °C / Inert atmosphere

6.2: 16 h / 0 °C / Inert atmosphere

7.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 2.25 h / 0 - 20 °C / Inert atmosphere

8.1: N-iodo-succinimide; 2,6-dimethylpyridine / 0.03 h / 0 °C / Inert atmosphere

9.1: dichloro bis(acetonitrile) palladium(II); triphenyl-arsane; Tetrabutylammoniumsalz der Diphenylphosphinsaeure / N,N-dimethyl-formamide / 20 h / 20 °C / Darkness; Inert atmosphere; Schlenk technique

9.2: 0.08 h / Inert atmosphere; Darkness; Schlenk technique

9.3: 18 h / Inert atmosphere; Schlenk technique; Darkness

10.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / N,N-dimethyl-formamide / 16 h / 20 °C / Darkness; Inert atmosphere

With 2,6-dimethylpyridine; dichloro bis(acetonitrile) palladium(II); (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium dihydrogenphosphate; N-iodo-succinimide; n-butyllithium; trimethylamine-N-oxide; triphenyl-arsane; tris(dimethylamino)sulfonium trimethylsilyldifluoride; dihydrogen peroxide; copper(l) cyanide; Dess-Martin periodane; triphenylphosphine; Tetrabutylammoniumsalz der Diphenylphosphinsaeure; potassium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: |Corey-Fuchs Alkyne Synthesis / 1.2: |Corey-Fuchs Alkyne Synthesis;

DOI:10.1002/anie.201702189

upstream raw materials:

(2S,4S)-2,4-dimethylhexanal

(3S,5S)-1,1-dibromo-3,5-dimethyl-1-heptene

(2E,4E)-5-bromopenta-2,4-dienal

(2S,4S)-N-[(1'R,2'R)-2'-hydroxy-1'-methyl-2'-phenylethyl]-N-methyl-2,4-dimethylhexanamide

Refernces

Polyunsaturated C-Glycosidic 4-Hydroxy-2-pyrone Derivatives: Total Synthesis Shows that Putative Orevactaene Is Likely Identical with Epipyrone A

10.1002/anie.201702189

The research focuses on the total synthesis of polyunsaturated C-glycosidic 4-hydroxy-2-pyrone derivatives, specifically orevactaene and epipyrone A. These compounds were initially thought to have different structures, but the study reveals that orevactaene is likely identical to epipyrone A. Key chemicals and reactions involved in the research include the use of tungsten and gold catalysis for the formation of the bicyclic core of orevactaene through alkyne cycloisomerization, and the use of heterobimetallic polyunsaturated modules for selective and consecutive cross-coupling. Other important chemicals and reactions include the use of d-arabinose as a starting material, Wittig olefination, dihydroxylation, DIBAL-H reduction, and various other transformations and coupling reactions to assemble the complex structures. The research also involves the preparation of different isomers and the use of spectroscopic techniques to confirm the structures and stereochemistry of the synthesized compounds.

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 197631-20-2 (2Z,3E,5E,7E,9E,11E,13E)-14-[(7S,8R,9R)-7,8-dihydroxy-5-oxo-9-(1,2,3-t rihydroxypropyl)-4,10-dioxabicyclo[4.4.0]deca-2,11-dien-3-yl]-2-(2,4-d imethylhexylidene)-4-methyl-tetradeca-3,5,7,9,11,13-hexaenoic acid

Send

Send

Metric Ton KG G Pound L ML

Send

Send