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

Base Information

• Chemical Name: (1S,3Z,4S,5S,6R)-5-ethenyl-5-hydroxy-3-(hydroxymethylene)-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one
• CAS No.: 380621-71-6
• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.381
• Mol file: 380621-71-6.mol

Synonyms:(1S,3Z,4S,5S,6R)-5-ethenyl-5-hydroxy-3-(hydroxymethylene)-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one

Chemical Property of (1S,3Z,4S,5S,6R)-5-ethenyl-5-hydroxy-3-(hydroxymethylene)-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3Z,4S,5S,6R)-5-ethenyl-5-hydroxy-3-(hydroxymethylene)-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one

There total 12 articles about (1S,3Z,4S,5S,6R)-5-ethenyl-5-hydroxy-3-(hydroxymethylene)-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one 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%

(1S,4S,5S,6R)-5-ethenyl-5-hydroxy-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one (380621-70-5) + formic acid ethyl ester (109-94-4) → (1S,3Z,4S,5S,6R)-5-ethenyl-5-hydroxy-3-(hydroxymethylene)-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one (380621-71-6)

Guidance literature:

(1S,4S,5S,6R)-5-ethenyl-5-hydroxy-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

formic acid ethyl ester; In tetrahydrofuran; at 0 - 18 ℃; for 2h;

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,3Z,4S,5S,6R)-5-ethenyl-5-hydroxy-3-(hydroxymethylene)-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one (380621-71-6)

Guidance literature:

Multi-step reaction with 11 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

With 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; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; acetone; benzene;

DOI:10.1039/b105376k

Reference yield:

(2S,3aS,7aS)-4-bromo-3a,7a-dihydro-2-phenyl-1,3-benzodioxole (380621-87-4) → (1S,3Z,4S,5S,6R)-5-ethenyl-5-hydroxy-3-(hydroxymethylene)-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one (380621-71-6)

Guidance literature:

Multi-step reaction with 10 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

With 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; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; acetone; benzene;

DOI:10.1039/b105376k

upstream raw materials:

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

formic acid ethyl ester

p-Anisaldehyde dimethyl acetal

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

Downstream raw materials:

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

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