ethyl <(1'R,2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate

Base Information

• Chemical Name: ethyl <(1'R,2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate
• CAS No.: 142980-90-3
• Molecular Formula: C₁₇H₃₄O₄Si
• Molecular Weight: 330.54
• Mol file: 142980-90-3.mol

Synonyms:ethyl <(1'R,2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate

Chemical Property of ethyl <(1'R,2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl <(1'R,2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate

There total 6 articles about ethyl <(1'R,2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate 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: 90.0%

tert-butyldimethylsilyl chloride (18162-48-6) + ethyl <(1'R,2'S,5'S)-1',5-'dihydroxy-2'-methylcyclohexyl>ethanoate (142980-89-0) → ethyl <(1'R,2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate (142980-90-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 24h;

DOI:10.1021/jo00045a038

Reference yield:

ethyl <(2'R,5'R)-6-hydroperoxy-2',6-'dimethylbicyclo<3.2.1>-7'-oxaoctyl>ethanoate (142980-87-8,143060-75-7) → ethyl <(2'R,5'R)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate (142980-90-3)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine, DMAP / CH₂Cl₂ / a) 0 deg C, 1 h, b) r.t., 2 h, c) reflux, 12 h

2: 0.2 M NaOEt / ethanol / 3 h / 0 °C

3: imidazole / dimethylformamide / 24 h

With pyridine; 1H-imidazole; dmap; sodium ethanolate; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00045a038

Reference yield:

ethyl <(1'R,2'S,5'S)-6-hydroperoxy-2',6-'dimethylbicyclo<3.2.1>-7'-oxaoctyl>ethanoate (142980-87-8,143060-75-7) → ethyl <(1'R,2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate (142980-90-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / pyridine, DMAP / CH₂Cl₂ / a) 0 deg C, 1 h, b) r.t., 2 h, c) reflux, 12 h

2: 87 percent / 0.2 M NaOEt / ethanol / 3 h / 0 °C

3: 90 percent / imidazole / dimethylformamide / 24 h

With pyridine; 1H-imidazole; dmap; sodium ethanolate; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00045a038

upstream raw materials:

tert-butyldimethylsilyl chloride

ethyl <(2'R,5'R)-1',5-'dihydroxy-2'-methylcyclohexyl>ethanoate

ethyl <(2'R,5'R)-6-hydroperoxy-2',6-'dimethylbicyclo<3.2.1>-7'-oxaoctyl>ethanoate

ethyl <(2'R,5'R)-5'-acetoxy-1'-hydroxy-2'-methylcyclohexyl>ethanoate

Downstream raw materials:

dihydrotachysterol₂ tert-butyldimethylsilyl ether

25-hydroxydihydrotachysterol₂

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

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