3',4-O-Dimethylcedrusin

Base Information

• Chemical Name: 3',4-O-Dimethylcedrusin
• CAS No.: 127179-41-3
• Molecular Formula: C21H26 O6
• Molecular Weight: 374.42754
• DSSTox Substance ID: DTXSID70155455
• Nikkaji Number: J1.001.918D
• Wikidata: Q83023372
• Metabolomics Workbench ID: 136543
• ChEMBL ID: CHEMBL464374
• Mol file: 127179-41-3.mol

Synonyms:2-(3',4'-dimethoxyphenyl)-2,3-dihydro-3-hydroxymethyl-7-methoxybenzofuran-5-propan-1-ol;3',4-O-dimethylcedrusin;4-O-methyldihydrodehydrodiconiferyl alcohol

Chemical Property of 3',4-O-Dimethylcedrusin

Chemical Property:

• Boiling Point: 522.4°Cat760mmHg
• Flash Point: 269.7°C
• PSA: 77.38000
• Density: 1.203g/cm³
• LogP: 2.84690
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 374.17293854
• Heavy Atom Count: 27
• Complexity: 446

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2C(C3=C(O2)C(=CC(=C3)CCCO)OC)CO)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@@H]2[C@H](C3=C(O2)C(=CC(=C3)CCCO)OC)CO)OC

Technology Process of 3',4-O-Dimethylcedrusin

There total 9 articles about 3',4-O-Dimethylcedrusin 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: 74.0%

hierochin B (215228-14-1) → 3',4-di-O-methylcedrusin (127179-41-3)

Guidance literature:

With hydrogen; PtO₂/C; In ethanol; for 1h;

DOI:10.1016/S0040-4020(98)00725-X

Reference yield:

(E)-3-[(2R*,3S*)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(3-methoxy-4-methoxymethoxyphenyl)-1-benzofuran-5-yl]-2-propenal (118799-85-2) → 3',4-di-O-methylcedrusin (127179-41-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 5 mg / DIPEA / CH₂Cl₂ / 3 h / Ambient temperature

2: 88 percent / K₂CO₃ / methanol; tetrahydrofuran / 0.5 h

3: 90 percent / aq. HCl / methanol / 3 h

4: 89 percent / K₂CO₃ / acetone / 1 h

5: 84 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 1 h / 0 °C

6: 74 percent / H₂ / PtO₂/C / ethanol / 1 h

With hydrogenchloride; lithium aluminium tetrahydride; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; PtO₂/C; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetone;

DOI:10.1016/S0040-4020(98)00725-X

Reference yield:

(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (2S,3R)-7-methoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-3-ylmethyl ester (215227-86-4) → 3',4-di-O-methylcedrusin (127179-41-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / K₂CO₃ / methanol; tetrahydrofuran / 0.5 h

2: 90 percent / aq. HCl / methanol / 3 h

3: 89 percent / K₂CO₃ / acetone / 1 h

4: 84 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 1 h / 0 °C

5: 74 percent / H₂ / PtO₂/C / ethanol / 1 h

With hydrogenchloride; lithium aluminium tetrahydride; hydrogen; potassium carbonate; PtO₂/C; In tetrahydrofuran; methanol; diethyl ether; ethanol; acetone;

DOI:10.1016/S0040-4020(98)00725-X

upstream raw materials:

diazomethane

2α,3β-7-O-methylcedrusin

hierochin B

(E)-3-[(2R*,3S*)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(3-methoxy-4-methoxymethoxyphenyl)-1-benzofuran-5-yl]-2-propenal

Downstream raw materials:

dihydrodehydrodiisoeugenol methyl ether

2-[(R)-2-(3,4-Dimethoxy-phenyl)-1-methyl-ethyl]-6-methoxy-4-propyl-phenol

C₃₃H₃₄O₁₀S₂

Refernces

• 1、 Lemiere, Guy,Gao, Mei,Groot, Alex De,Dommisse, Roger,Lepoivre, Josef,et al.. "3',4-Di-O-methylcedrusin: synthesis, resolution and absolute configuration". . p. 1775 - 1780. Retrieved 2007/10/02.