(2R,3S,3aR,5R,6S)-3a-Allyl-5,6,7a-trimethoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran

Base Information

• Chemical Name: (2R,3S,3aR,5R,6S)-3a-Allyl-5,6,7a-trimethoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran
• CAS No.: 86534-76-1
• Molecular Formula: C₂₄H₃₆O₇
• Molecular Weight: 436.546
• Mol file: 86534-76-1.mol

Synonyms:(2R,3S,3aR,5R,6S)-3a-Allyl-5,6,7a-trimethoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran

Chemical Property of (2R,3S,3aR,5R,6S)-3a-Allyl-5,6,7a-trimethoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,3aR,5R,6S)-3a-Allyl-5,6,7a-trimethoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran

There total 1 articles about (2R,3S,3aR,5R,6S)-3a-Allyl-5,6,7a-trimethoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran 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: 75.0%

(2R,3S,3aR,5R,6S)-3a-Allyl-7a-methoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran-5,6-diol (86534-75-0) + methyl iodide (74-88-4) → (2R,3S,3aR,5R,6S)-3a-Allyl-5,6,7a-trimethoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran (86534-76-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 45 ℃; for 1h;

DOI:10.1016/S0040-4039(00)86382-0

Reference yield:

(2R,3S,3aR,5R,6S)-3a-Allyl-5,6,7a-trimethoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran (86534-76-1) → Methanesulfonic acid (2R,3S,3aR,5R,6S)-3a-allyl-7a-hydroxy-5-methoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran-6-yl ester

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; aq. HCl / 0.42 h / Ambient temperature

2: 64 percent / tetrahydrofuran; aq. HCl / 6 h / Ambient temperature

3: N(C₂H₅)3 / tetrahydrofuran / 1 h / -15 - 5 °C

With triethylamine; In tetrahydrofuran; hydrogenchloride;

DOI:10.1016/S0040-4039(00)86382-0

Reference yield:

(2R,3S,3aR,5R,6S)-3a-Allyl-5,6,7a-trimethoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran (86534-76-1) → d,l-megaphone (64332-37-2,78148-79-5,96895-52-2,106973-35-7)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran; aq. HCl / 0.42 h / Ambient temperature

2: 64 percent / tetrahydrofuran; aq. HCl / 6 h / Ambient temperature

3: N(C₂H₅)3 / tetrahydrofuran / 1 h / -15 - 5 °C

4: 71 percent / DBU / benzene / room temp., 3 h, then 60 deg C, 2 h

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; hydrogenchloride; benzene;

DOI:10.1016/S0040-4039(00)86382-0

upstream raw materials:

(2R,3S,3aR,5R,6S)-3a-Allyl-7a-methoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran-5,6-diol

methyl iodide

Downstream raw materials:

(2R,3S,3aR,5R,6S)-3a-Allyl-5,6-dimethoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-hexahydro-benzofuran-7a-ol

(2R,3S,3aR,5R,6S)-3a-Allyl-5-methoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-hexahydro-benzofuran-6,7a-diol

d,l-megaphone