(1S,2S,3R,4R,5R,6E)-2-ethenyl-6-(2'-methoxyethoxymethoxymethylene)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octane-2,5-diol

Base Information

• Chemical Name: (1S,2S,3R,4R,5R,6E)-2-ethenyl-6-(2'-methoxyethoxymethoxymethylene)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octane-2,5-diol
• CAS No.: 380621-74-9
• Molecular Formula: C₂₃H₃₂O₇
• Molecular Weight: 420.503
• Mol file: 380621-74-9.mol

Synonyms:(1S,2S,3R,4R,5R,6E)-2-ethenyl-6-(2'-methoxyethoxymethoxymethylene)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octane-2,5-diol

Chemical Property of (1S,2S,3R,4R,5R,6E)-2-ethenyl-6-(2'-methoxyethoxymethoxymethylene)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octane-2,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4R,5R,6E)-2-ethenyl-6-(2'-methoxyethoxymethoxymethylene)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octane-2,5-diol

There total 14 articles about (1S,2S,3R,4R,5R,6E)-2-ethenyl-6-(2'-methoxyethoxymethoxymethylene)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octane-2,5-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: 85.0%

(1S,3E,4S,5S,6R)-5-ethenyl-5-hydroxy-3-(2'-methoxyethoxymethoxymethylene)-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one (380621-72-7) → (1S,2S,3R,4R,5R,6E)-2-ethenyl-6-(2'-methoxyethoxymethoxymethylene)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octane-2,5-diol (380621-74-9) + (1S,2S,3R,4R,5S,6E)-2-ethenyl-6-(2'-methoxyethoxymethoxymethylene)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octane-2,5-diol

Guidance literature:

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; In ethanol; at 0 ℃; for 1h;

DOI:10.1039/b105376k

Reference yield:

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene (67451-62-1,82683-92-9,132958-32-8,130792-45-9) → (1S,2S,3R,4R,5R,6E)-2-ethenyl-6-(2'-methoxyethoxymethoxymethylene)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octane-2,5-diol (380621-74-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 14.1 g / (1S)-(+)-camphor-10-sulfonic acid monohydrate / CH₂Cl₂ / 1 h / -20 - 10 °C

2.1: 91 percent / TMSOTf / CH₂Cl₂ / 24 h / 18 °C

3.1: 97 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / 26 h / 18 °C

4.1: 97 percent / (1S)-(+)-camphor-10-sulfonic acid monohydrate / CH₂Cl₂ / 3 h / -20 °C

5.1: 70 percent / DIBAL-H / CH₂Cl₂; hexane / 10 h / -50 - 0 °C

6.1: 70 percent / Bu₃SnH; AIBN / benzene / 6 h / 18 °C / Irradiation

7.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 18 °C

8.1: 85 percent / tetrahydrofuran / 3 h / -40 °C

9.1: 90 percent / pyridinium toluene-p-sulfonate; H₂O / acetone / 24 h / Heating

10.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

10.2: 75 percent / tetrahydrofuran / 2 h / 0 - 18 °C

11.1: 80 percent / DBU / dimethylformamide / 5 h / -55 - -20 °C

12.1: 85 percent / NaBH₄; CeCl₃; 2,6-lutidine / ethanol / 1 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; (+)-camphor-10-sulfonic acid monohydrate; water; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 13.1: Luche reduction;

DOI:10.1039/b105376k

Reference yield:

(2S,3aS,7aS)-4-bromo-3a,7a-dihydro-2-phenyl-1,3-benzodioxole (380621-87-4) → (1S,2S,3R,4R,5R,6E)-2-ethenyl-6-(2'-methoxyethoxymethoxymethylene)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octane-2,5-diol (380621-74-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 91 percent / TMSOTf / CH₂Cl₂ / 24 h / 18 °C

2.1: 97 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / 26 h / 18 °C

3.1: 97 percent / (1S)-(+)-camphor-10-sulfonic acid monohydrate / CH₂Cl₂ / 3 h / -20 °C

4.1: 70 percent / DIBAL-H / CH₂Cl₂; hexane / 10 h / -50 - 0 °C

5.1: 70 percent / Bu₃SnH; AIBN / benzene / 6 h / 18 °C / Irradiation

6.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 18 °C

7.1: 85 percent / tetrahydrofuran / 3 h / -40 °C

8.1: 90 percent / pyridinium toluene-p-sulfonate; H₂O / acetone / 24 h / Heating

9.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

9.2: 75 percent / tetrahydrofuran / 2 h / 0 - 18 °C

10.1: 80 percent / DBU / dimethylformamide / 5 h / -55 - -20 °C

11.1: 85 percent / NaBH₄; CeCl₃; 2,6-lutidine / ethanol / 1 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; (+)-camphor-10-sulfonic acid monohydrate; water; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 12.1: Luche reduction;

DOI:10.1039/b105376k

upstream raw materials:

(1S,3E,4S,5S,6R)-5-ethenyl-5-hydroxy-3-(2'-methoxyethoxymethoxymethylene)-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one

p-Anisaldehyde dimethyl acetal

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

(2S,3aS,7aS)-4-bromo-3a,7a-dihydro-2-phenyl-1,3-benzodioxole