3-[(E)-1,5-dihydroxy-4-methylpent-3-enyl]-4-hydroxy-7-methoxy-2,3,8-trimethyl-2H-benzo[g][1]benzofuran-6,9-dione

Base Information

• Chemical Name: 3-[(E)-1,5-dihydroxy-4-methylpent-3-enyl]-4-hydroxy-7-methoxy-2,3,8-trimethyl-2H-benzo[g][1]benzofuran-6,9-dione
• CAS No.: 125224-54-6
• Molecular Formula: C22H26 O7
• Molecular Weight: 402.4376
• DSSTox Substance ID: DTXSID001037220
• Mol file: 125224-54-6.mol

Synonyms:furaquinocin A

Chemical Property of 3-[(E)-1,5-dihydroxy-4-methylpent-3-enyl]-4-hydroxy-7-methoxy-2,3,8-trimethyl-2H-benzo[g][1]benzofuran-6,9-dione

Chemical Property:

• Boiling Point: 673.5°Cat760mmHg
• Flash Point: 235.9°C
• PSA: 113.29000
• Density: 1.34g/cm³
• LogP: 2.41980
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 402.16785316
• Heavy Atom Count: 29
• Complexity: 754

Purity/Quality:

95% ^*data from raw suppliers

FURAQUINOCIN B 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C2=C(C=C3C(=C2O1)C(=O)C(=C(C3=O)OC)C)O)(C)C(CC=C(C)CO)O
• Isomeric SMILES: CC1C(C2=C(C=C3C(=C2O1)C(=O)C(=C(C3=O)OC)C)O)(C)C(C/C=C(\C)/CO)O

Technology Process of 3-[(E)-1,5-dihydroxy-4-methylpent-3-enyl]-4-hydroxy-7-methoxy-2,3,8-trimethyl-2H-benzo[g][1]benzofuran-6,9-dione

There total 25 articles about 3-[(E)-1,5-dihydroxy-4-methylpent-3-enyl]-4-hydroxy-7-methoxy-2,3,8-trimethyl-2H-benzo[g][1]benzofuran-6,9-dione 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: 79.0%

(2R,3S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(E)-(R)-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-pent-3-enyl]-7-methoxy-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-6,9-dione (217486-65-2) → furaquinocin B (125224-54-6)

Guidance literature:

With 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2.5h;

DOI:10.1021/ja982403t

Reference yield: 61.0%

(2R,3R)-3-[(R)-(E)-bis(tert-butyldimethylsilanyloxy)methylpent-3-enyl]-7-methoxy-2,3,8-trimethyl-4-triisopropylsilanyloxy-2,3-dihydronaphtho[1,2-b]furan-6,9-dione (628299-83-2) → furaquinocin B (125224-54-6)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 20h;

DOI:10.1021/ja0364118

Reference yield:

(2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-carbaldehyde (217486-32-3) → furaquinocin B (125224-54-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) hexane, DMSO, RT, 40 min, 2.) hexane, DMSO, RT, 6 d

2: 1.) n-BuLi, 2.) BF₃*OEt₂ / 1.) THF, hexane, -78 deg C, 3 h, 2.) THF, hexane, -78 deg C, 5 h

3: 1 M aq. H₂SO₄ / 1,2-dimethoxy-ethane / 3 h / 75 °C

4: Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

5: 1,4-cyclohexadiene / 10percent Pd/C / ethanol / 0.33 h / 45 °C

6: DDQ, phosphate buffer (pH 7) / CH₂Cl₂; 2-methyl-propan-2-ol / 0 °C

7: 79 percent / TBAF, 4 Angstroem molecular sieves / tetrahydrofuran / 2.5 h

With n-butyllithium; phosphate buffer; cyclohexa-1,4-diene; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja982403t

upstream raw materials:

(2R,3S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(E)-(R)-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-pent-3-enyl]-7-methoxy-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-6,9-dione

(2R,3R)-3-[(R)-(E)-bis(tert-butyldimethylsilanyloxy)methylpent-3-enyl]-7-methoxy-2,3,8-trimethyl-4-triisopropylsilanyloxy-2,3-dihydronaphtho[1,2-b]furan-6,9-dione

2-iodoresorcinol

(2R,3S)-4-hydroxy-2,3-dimethyl-2,3-dihydro-benzofuran-3-carbonitrile

Downstream raw materials:

C₅₂H₄₇F₉O₁₃

C₅₂H₄₇F₉O₁₃

C₃₆H₃₄O₉

C₃₆H₃₂O₈