(-)-Isomegaphone

Base Information

• Chemical Name: (-)-Isomegaphone
• CAS No.: 96895-52-2
• Molecular Formula: C₂₂H₃₀O₆
• Molecular Weight: 390.477
• Mol file: 96895-52-2.mol

Synonyms:

Chemical Property of (-)-Isomegaphone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-Isomegaphone

There total 19 articles about (-)-Isomegaphone 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: 71.0%

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 → d,l-megaphone (64332-37-2,78148-79-5,96895-52-2,106973-35-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; room temp., 3 h, then 60 deg C, 2 h;

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

Reference yield: 46.0%

(S)-2-((1R,5R)-1-Allyl-5-methoxy-2-oxo-cyclohex-3-enyl)-propionaldehyde (96851-93-3) + 1-lithio-3,4,5-trimethoxybenzene (81952-68-3) → (-)-Isomegaphone (96895-52-2) + (-)-Megaphone (64332-37-2)

Guidance literature:

In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃;

DOI:10.1016/S0040-4039(00)61960-3

Reference yield:

(2β,3β,3aα,5β)-3,3a,4,5-tetrahydro-5-methoxy-3-methyl-3a-(2-propenyl)-2-(3,4,5-trimethoxyphenyl)-6(2H)-benzofuranone (76202-43-2,78108-41-5,90898-97-8,112455-82-0,137491-87-3) → d,l-megaphone (64332-37-2,78148-79-5,96895-52-2,106973-35-7)

Guidance literature:

With diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; Yield given. Multistep reaction; 1.) THF, hexane, 45 min, 2.) THF, -55 - -60 deg C, 15 min;

DOI:10.1021/ja00400a039

upstream raw materials:

(2β,3β,3aα,5β)-3,3a,4,5-tetrahydro-5-methoxy-3-methyl-3a-(2-propenyl)-2-(3,4,5-trimethoxyphenyl)-6(2H)-benzofuranone

(2β,3β,3aα,5β)-3,3a,4,5-tetrahydro-5-methoxy-3-methyl-3a-<3-<(methylsulfonyl)oxy>propyl>-2-(3,4,5-trimethoxyphenyl)-6(2H)-benzofuranone

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

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