(1R,2S)-2-methyl-3-methylene-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)butane-1,4-diol

Base Information

• Chemical Name: (1R,2S)-2-methyl-3-methylene-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)butane-1,4-diol
• CAS No.: 1441119-51-2
• Molecular Formula: C₂₃H₂₈O₈
• Molecular Weight: 432.471
• Mol file: 1441119-51-2.mol

Synonyms:(1R,2S)-2-methyl-3-methylene-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)butane-1,4-diol

Chemical Property of (1R,2S)-2-methyl-3-methylene-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)butane-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-2-methyl-3-methylene-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)butane-1,4-diol

There total 6 articles about (1R,2S)-2-methyl-3-methylene-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)butane-1,4-diol 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: 92.0%

(1R,2S)-2-methyl-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)-3-[(triisopropylsilyloxy)methyl]but-3-en-1-ol (1441119-49-8) → (1R,2S)-2-methyl-3-methylene-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)butane-1,4-diol (1441119-51-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.201201247

Reference yield:

6-bromo-7-methoxybenzo[1,3]dioxole-5-carboxylic acid ethyl ester (418755-58-5) → (1R,2S)-2-methyl-3-methylene-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)butane-1,4-diol (1441119-51-2)

Guidance literature:

Multi-step reaction with 5 steps

1: diisobutylaluminium hydride / toluene / -78 °C

2: CyJohnPhos; potassium phosphate; palladium diacetate / toluene / 80 °C / Inert atmosphere

3: potassium tert-butylate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

4: n-butyllithium; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] / diethyl ether; hexane / 8 h / -78 °C / Inert atmosphere

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With potassium phosphate; n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; palladium diacetate; diisobutylaluminium hydride; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; CyJohnPhos; In tetrahydrofuran; diethyl ether; hexane; toluene; 2: |Suzuki Coupling / 3: |Williamson Ether Synthesis / 4: |[2,3]-Wittig Rearrangement;

DOI:10.1002/ejoc.201201247

Reference yield:

ethyl (3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)carboxylate (1441119-45-4) → (1R,2S)-2-methyl-3-methylene-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)butane-1,4-diol (1441119-51-2)

Guidance literature:

Multi-step reaction with 4 steps

1: diisobutylaluminium hydride / hexane; toluene / 1.5 h / -78 °C / Inert atmosphere

2: potassium tert-butylate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

3: n-butyllithium; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] / diethyl ether; hexane / 8 h / -78 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; In tetrahydrofuran; diethyl ether; hexane; toluene; 2: |Williamson Ether Synthesis / 3: |[2,3]-Wittig Rearrangement;

DOI:10.1002/ejoc.201201247

upstream raw materials:

(6-bromo-7-methoxybenzo[d][1,3] dioxol-5-yl-)methanol

ethyl (3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)carboxylate

(E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene

(1R,2S)-2-methyl-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)-3-[(triisopropylsilyloxy)methyl]but-3-en-1-ol

Downstream raw materials:

(-)-eupomatilone 1