Methanesulfonic acid, trifluoro-, (3S,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-1-cyclohexen- 1-yl ester

Base Information

• Chemical Name: Methanesulfonic acid, trifluoro-, (3S,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-1-cyclohexen- 1-yl ester
• CAS No.: 849676-22-8
• Molecular Formula: C13H23F3O5SSi
• Molecular Weight: 376.469
• Mol file: 849676-22-8.mol

Synonyms:

Chemical Property of Methanesulfonic acid, trifluoro-, (3S,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-1-cyclohexen- 1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid, trifluoro-, (3S,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-1-cyclohexen- 1-yl ester

There total 2 articles about Methanesulfonic acid, trifluoro-, (3S,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-1-cyclohexen- 1-yl ester 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: 68.0%

(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-3-trifluoromethanesulfonyloxy-cyclohex-2-enyl ester (849676-23-9) → Trifluoro-methanesulfonic acid (3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester (849676-22-8)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -40 ℃; for 16h;

DOI:10.1021/jo047858h

Reference yield:

4-(tert-butyldimethylsilyloxy)cyclohexanone (55145-45-4) → Trifluoro-methanesulfonic acid (3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester (849676-22-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / DIBAL / toluene; tetrahydrofuran / 16 h / -40 °C

With diisobutylaluminium hydride; In tetrahydrofuran; toluene;

DOI:10.1021/jo047858h

Reference yield:

Trifluoro-methanesulfonic acid (3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester (849676-22-8) → (3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 480 mg / Ag₂O / diethyl ether / 3 h / 40 °C

2: 322 mg / PPh₃; Et₃N / Pd(OAc)2 / dimethylformamide / 16 h / 20 °C

With triethylamine; triphenylphosphine; silver(l) oxide; palladium diacetate; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo047858h

upstream raw materials:

(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-3-trifluoromethanesulfonyloxy-cyclohex-2-enyl ester

4-(tert-butyldimethylsilyloxy)cyclohexanone

Downstream raw materials:

Trifluoro-methanesulfonic acid (3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohex-1-enyl ester