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

Base Information

Chemical Name:(1S,4S,5S,6R)-5-ethenyl-5-hydroxy-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one ethylene acetal
CAS No.:380621-69-2
Molecular Formula:C₂₀H₂₆O₅
Molecular Weight:346.423
Hs Code.:

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

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

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

There total 10 articles about (1S,4S,5S,6R)-5-ethenyl-5-hydroxy-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one ethylene acetal 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%

: 1826-67-1
vinyl magnesium bromide

: 736980-44-2
(1S,3R,4S)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2,5-dione 5-(ethylene acetal)

: 380621-69-2
(1S,4S,5S,6R)-5-ethenyl-5-hydroxy-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one ethylene acetal

Guidance literature:: In tetrahydrofuran; at -40 ℃; for 3h;
DOI:10.1039/b105376k

Reference yield:

: 67451-62-1,82683-92-9,132958-32-8,130792-45-9
cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

: 380621-69-2
(1S,4S,5S,6R)-5-ethenyl-5-hydroxy-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one ethylene acetal

Guidance literature:: Multi-step reaction with 9 steps

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

2: 91 percent / TMSOTf / CH₂Cl₂ / 24 h / 18 °C

3: 97 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / 26 h / 18 °C

4: 97 percent / (1S)-(+)-camphor-10-sulfonic acid monohydrate / CH₂Cl₂ / 3 h / -20 °C

5: 70 percent / DIBAL-H / CH₂Cl₂; hexane / 10 h / -50 - 0 °C

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

7: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 18 °C

8: 85 percent / tetrahydrofuran / 3 h / -40 °C

With oxalyl dichloride; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; (+)-camphor-10-sulfonic acid monohydrate; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; benzene;
DOI:10.1039/b105376k

Reference yield:

: 380621-87-4
(2S,3aS,7aS)-4-bromo-3a,7a-dihydro-2-phenyl-1,3-benzodioxole

: 380621-69-2
(1S,4S,5S,6R)-5-ethenyl-5-hydroxy-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one ethylene acetal

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / TMSOTf / CH₂Cl₂ / 24 h / 18 °C

2: 97 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / 26 h / 18 °C

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

4: 70 percent / DIBAL-H / CH₂Cl₂; hexane / 10 h / -50 - 0 °C

5: 70 percent / Bu₃SnH; AIBN / benzene / 6 h / 18 °C / Irradiation

6: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 18 °C

7: 85 percent / tetrahydrofuran / 3 h / -40 °C

With oxalyl dichloride; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; (+)-camphor-10-sulfonic acid monohydrate; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; benzene;
DOI:10.1039/b105376k