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

Base Information

• Chemical Name: (1R,2S,4S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol
• CAS No.: 94597-66-7
• Molecular Formula: C₂₂H₃₆O₂SeSi
• Molecular Weight: 439.572
• Mol file: 94597-66-7.mol

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

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

There total 6 articles about (1R,2S,4S)-1-[(tert-butyldimethylsilyloxy)methyl]-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: 46.0%

diphenyl diselenide (1666-13-3) + (S)-tert-butyldimethyl[(4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methoxy]silane (94597-63-4) → C22H36O2SeSi + (1S,2R,4S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol (94597-65-6) + (1R,2S,4S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol (94597-66-7)

Guidance literature:

diphenyl diselenide; With sodium tetrahydroborate; In ethanol; at 20 ℃; for 1h;

(S)-tert-butyldimethyl[(4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methoxy]silane; In ethanol; at 65 ℃;

Reference yield:

(-)-perillyl alcohol (536-59-4,18457-55-1) → (1R,2S,4S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol (94597-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1: VO(AcAc)2, t-BuOOH / toluene; 2-methyl-propan-2-ol / 10 h / Ambient temperature

2: 100 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: NaBH₄ / ethanol / 24 h / Heating

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

DOI:10.1021/jo00205a015

Reference yield:

((4S)-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methanol (190718-78-6) → (1R,2S,4S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol (94597-66-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: NaBH₄ / ethanol / 24 h / Heating

With 1H-imidazole; sodium tetrahydroborate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00205a015

upstream raw materials:

diphenyl diselenide

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

(-)-perillyl alcohol

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

Downstream raw materials:

(S)-1-Hydroxymethyl-4-isopropenyl-2-phenylselanyl-cyclohexanol

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

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

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