(2E)-2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanol

Base Information

• Chemical Name: (2E)-2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanol
• CAS No.: 142980-92-5
• Molecular Formula: C₁₅H₃₀O₂Si
• Molecular Weight: 270.488
• Mol file: 142980-92-5.mol

Synonyms:(2E)-2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanol

Chemical Property of (2E)-2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E)-2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanol

There total 10 articles about (2E)-2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanol 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: 99.0%

(2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate (142980-91-4) → (2E)-2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanol (142980-92-5)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 1h;

DOI:10.1021/jo00045a038

Reference yield:

(-)-dihydrocarvone (5524-05-0,619-02-3) → (2E)-2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanol (142980-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) NaH / 1) THF, a) -20 deg C, 1 h, b) r.t., 2 h, 2) r.t., 24 h

3: 95 percent / imidazole / dimethylformamide

4: 97 percent / DIBAL-H / toluene / 1 h / -78 °C

With 1H-imidazole; sodium hydride; diisobutylaluminium hydride; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)85618-0

Reference yield:

[(2S,5S)-5-Hydroxy-2-methyl-cyclohex-(E)-ylidene]-acetic acid ethyl ester (145260-95-3) → (2E)-2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanol (142980-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / imidazole / dimethylformamide

2: 97 percent / DIBAL-H / toluene / 1 h / -78 °C

With 1H-imidazole; diisobutylaluminium hydride; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)85618-0

upstream raw materials:

(2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate

(S)-p-mentha-6,8-dien-2-one

(-)-dihydrocarvone

[(2S,5S)-5-Hydroxy-2-methyl-cyclohex-(E)-ylidene]-acetic acid ethyl ester

Downstream raw materials:

(2E)-<2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethyl>diphenylphosphine oxide

25-hydroxydihydrotachysterol₂

dihydrotachysterol₂ tert-butyldimethylsilyl ether

25-<(methoxymethyl)oxy>dihydrotachysterol₂ tert-butyldimethylsilyl ether