5-O-Methylhierochin D

Base Information

• Chemical Name: 5-O-Methylhierochin D
• CAS No.: 97465-82-2
• Molecular Formula: C20H22O6
• Molecular Weight: 358.391
• Mol file: 97465-82-2.mol

Synonyms:(+)-DEHYDRODICONIFERYL ALCOHOL

Chemical Property of 5-O-Methylhierochin D

Chemical Property:

• Boiling Point: 562.0±50.0 °C(Predicted)
• PKA: 9.79±0.35(Predicted)
• PSA: 88.38000
• Density: 1.292±0.06 g/cm3(Predicted)
• LogP: 2.62450

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 5-O-Methylhierochin D, also known as (+)-dehydrodiconiferyl alcohol, is a biologically active neolignan with demonstrated antioxidant and antitumor properties. It features a trans-disubstituted dihydrobenzofuran ring, synthesized through a rhodium-catalyzed intramolecular C–H insertion reaction, ensuring high diastereoselectivity. 5-O-Methylhierochin D has been characterized using spectroscopic methods such as NMR, IR, and HRMS, confirming its structural identity with natural samples.

Technology Process of 5-O-Methylhierochin D

There total 50 articles about 5-O-Methylhierochin D 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: 93.0%

(E)-methyl 3-<(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-1-benzofuran-5-yl>-1-propenoate (118799-80-7) → (±)-trans-(E)-4-(3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-7-methoxy-2,3-dihydrobenzofuran-2-yl)-2-methoxyphenol (4263-87-0,28199-68-0,60536-58-5,73135-77-0,86363-02-2,97465-82-2,112835-77-5,133318-47-5,138458-07-8,150407-42-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -20 ℃; for 2h;

Reference yield: 80.0%

(E)-3-[(2S,3R)-2,3-dihydro-2-(4'-hydroxy-3'-methoxyphenyl)-3-hydroxymethyl-7-methoxy-1-benzo[b]furan-5-yl]-2-propenal (215319-47-4) → (2S,3R)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-5-[(E)-3-hydroxy-1-propenyl]-3-hydroxymethyl-7-methoxybenzo[b]furan (97465-82-2)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; at 0 ℃; for 1h;

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

Reference yield: 65.0%

(2S,3R)-5-[(E)-2-ethoxycarbonylvinyl]-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzo[b]furan (352020-02-1) → (2S,3R)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-5-[(E)-3-hydroxy-1-propenyl]-3-hydroxymethyl-7-methoxybenzo[b]furan (97465-82-2)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 2h;

DOI:10.1271/bbb.65.1134

upstream raw materials:

coniferol

coniferal alcohol

ethyl caffeate

(E)-methyl 3-<(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-1-benzofuran-5-yl>-1-propenoate

Downstream raw materials:

hierochin B

2α,3β-7-O-methylcedrusin

dihydrodehydrodiconiferyl alcohol triacetate

(E)-3-[2-(4-Hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydrobenzo[b]furan-5-yl]-2-propenal

Refernces

A short-step asymmetric synthesis of dehydrodiconiferyl alcohol via C-H insertion reaction

10.1055/s-0031-1290658

The research focuses on the asymmetric total synthesis of (–)-dehydrodiconiferyl alcohol (1), a biologically active neolignan with potential antioxidant, antitumor, and other pharmacological properties. The synthesis involves a rhodium-catalyzed intramolecular C–H insertion reaction, which is key for achieving the trans-disubstituted dihydrobenzofuran ring with high diastereoselectivity. The process starts from commercially available guaiacol and includes 13 steps, utilizing various reactants such as aryl bromide 4, ortho-arylmethyloxy aryldiazoacetates, and chiral auxiliaries derived from mandelic acid. The experiments involve several reactions, including condensation, diazotransfer, C–H insertion, Heck reaction, and reductive manipulations. Analytical techniques used to characterize the synthesized compound include optical rotation, infrared spectroscopy (IR), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS), ensuring that the final product is spectroscopically identical to a natural sample of (–)-dehydrodiconiferyl alcohol.