(1R,2S,4S)-1-(hydroxymethyl)-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol

Base Information

• Chemical Name: (1R,2S,4S)-1-(hydroxymethyl)-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol
• CAS No.: 94619-47-3
• Molecular Formula: C₁₆H₂₂O₂Se
• Molecular Weight: 325.309
• Mol file: 94619-47-3.mol

Synonyms:(1R,2S,4S)-1-(hydroxymethyl)-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol

Chemical Property of (1R,2S,4S)-1-(hydroxymethyl)-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,4S)-1-(hydroxymethyl)-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol

There total 4 articles about (1R,2S,4S)-1-(hydroxymethyl)-2-(phenylselanyl)-4-(prop-1-en-2-yl)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: 98.0%

(1R,2S,4S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol (94597-66-7) → (1R,2S,4S)-1-(hydroxymethyl)-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol (94619-47-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 4h; Inert atmosphere;

Reference yield:

(S)-tert-butyldimethyl[(4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methoxy]silane (94597-63-4) → (1R,2S,4S)-1-(hydroxymethyl)-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol (94619-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium tetrahydroborate / ethanol / 1 h / 20 °C

1.2: 65 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 25 °C / Inert atmosphere

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; In tetrahydrofuran; ethanol;

Reference yield:

(-)-perillyl alcohol (536-59-4,18457-55-1) → (1R,2S,4S)-1-(hydroxymethyl)-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol (94619-47-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bis(acetylacetonate)oxovanadium; tert.-butylhydroperoxide / toluene; tert-butyl alcohol / 20 °C / Cooling with ice

2.1: 1H-imidazole / N,N-dimethyl-formamide / 0.17 h

2.2: 14 h

3.1: sodium tetrahydroborate / ethanol / 1 h / 20 °C

3.2: 65 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 25 °C / Inert atmosphere

With 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

upstream raw materials:

(-)-perillyl alcohol

((4S)-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methanol

(S)-tert-butyldimethyl[(4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methoxy]silane

(1R,2S,4S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol

Downstream raw materials:

[(1S,4S)-1-hydroxy-4-(prop-1-en-2-yl)cyclohex-2-enyl]methyl acetate

2-[(1S,6S)-3-(acetoxymethyl)-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentylresorcinol

[(1R,2S,4S)-1-hydroxy-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexyl]methyl acetate