(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

Base Information

• Chemical Name: (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
• CAS No.: 849676-23-9
• Molecular Formula: C₂₃H₃₅F₃O₈SSi
• Molecular Weight: 556.673
• Mol file: 849676-23-9.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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:

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 4-(tert-butyldimethylsilyloxy)cyclohexanone (55145-45-4) + (1S)-(-)-camphanic chloride (39637-74-6) → (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1R,6S)-6-(tert-butyl-dimethyl-silanyloxy)-3-trifluoromethanesulfonyloxy-cyclohex-2-enyl ester + (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)

Guidance literature:

Multistep reaction;

DOI:10.1021/jo047858h

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:

(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) → (3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 3 steps

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

2: 480 mg / Ag₂O / diethyl ether / 3 h / 40 °C

3: 322 mg / PPh₃; Et₃N / Pd(OAc)2 / dimethylformamide / 16 h / 20 °C

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

DOI:10.1021/jo047858h

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

4-(tert-butyldimethylsilyloxy)cyclohexanone

(1S)-(-)-camphanic chloride

Downstream raw materials:

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

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