(1R,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol

Base Information

• Chemical Name: (1R,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol
• CAS No.: 866398-11-0
• Molecular Formula: C₂₅H₄₂O₃
• Molecular Weight: 390.607
• Mol file: 866398-11-0.mol

Synonyms:(1R,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol

Chemical Property of (1R,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol

There total 26 articles about (1R,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol 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: 84.0%

3-{(7R,8R)-7-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-1,4-dioxaspiro[4,5]dec-8-yl}propan-1-ol (866398-09-6) → (1R,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol (866398-11-0) + (1S,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 3h;

DOI:10.1021/ol051570c

Reference yield: 33.0%

O-(1S,2S,4R)-4-hydroxy-2-[2-methoxy-4-(2-methyloctan-2-yl)phenyl]cyclohexyl S-methyl carbonodithioate (1374219-27-8) + allyltributylstanane (24850-33-7) → (1R,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol (866398-11-0)

Guidance literature:

O-(1S,2S,4R)-4-hydroxy-2-[2-methoxy-4-(2-methyloctan-2-yl)phenyl]cyclohexyl S-methyl carbonodithioate; allyltributylstanane; With 2,2'-azobis(isobutyronitrile); In benzene; at 80 ℃; for 12h; Inert atmosphere;

With borane-THF; at 0 - 20 ℃; for 1h;

With dihydrogen peroxide; sodium hydroxide; In water; at 20 ℃; for 1h; Cooling with ice;

DOI:10.1002/adsc.201100898

Reference yield:

trifluoromethanesulfonic acid 3-(1,1-dimethylheptyl)-5-methoxyphenyl ester (866398-19-8) → (1R,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol (866398-11-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / H₂; Et₃N / Pd/C / methanol / 120 h / 20 °C

2.1: 87 percent / Br₂; AcOH / 4 h / 20 °C

3.1: Mg; I₂ / tetrahydrofuran / 1.33 h / Heating

3.2: HMPA; CuBr*Me₂S / tetrahydrofuran / 2 h / -78 °C

4.1: 638 mg / TBAF / tetrahydrofuran / 0.5 h / 20 °C

5.1: 88 percent / TsOH / xylene / 1 h / Heating

6.1: TESOTf; 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6.2: 2,6-lutidine; H₂O / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 110 mg / NaBH₄ / methanol / 0.17 h / 0 °C

8.1: 84 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 3 h / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; bromine; iodine; triethylsilyl trifluoromethyl sulfonate; toluene-4-sulfonic acid; magnesium; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; xylene;

DOI:10.1021/ol051570c

upstream raw materials:

3-{(7R,8R)-7-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-1,4-dioxaspiro[4,5]dec-8-yl}propan-1-ol

trifluoromethanesulfonic acid 3-(1,1-dimethylheptyl)-5-methoxyphenyl ester

trifluoromethanesulfonic acid 4-(1,1-dimethylheptyl)-2,6-dimethoxyphenyl ester

(1R,4R,5R,8S)-4-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-8-methoxymethoxybicyclo[3.3.1]non-3-en-2-one

Downstream raw materials:

CP 55,940

Refernces

• 1、 Itagaki, Noriaki,Sugahara, Tsutomu,Iwabuchi, Yoshiharu. "Expedient synthesis of potent cannabinoid receptor agonist (-)-CP55,940". . p. 4181 - 4183. Retrieved 2007/10/03.