(4R,5S,6S,7S)-1-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-cycloheptene

Base Information

• Chemical Name: (4R,5S,6S,7S)-1-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-cycloheptene
• CAS No.: 906076-75-3
• Molecular Formula: C₂₇H₄₈O₄SSi₂
• Molecular Weight: 524.913
• Mol file: 906076-75-3.mol

Synonyms:(4R,5S,6S,7S)-1-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-cycloheptene

Chemical Property of (4R,5S,6S,7S)-1-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-cycloheptene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,6S,7S)-1-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-cycloheptene

There total 4 articles about (4R,5S,6S,7S)-1-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-cycloheptene 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: 97.0%

(1S,2S,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol (906076-73-1) + t-butyldimethylsiyl triflate (69739-34-0) → (4R,5S,6S,7S)-1-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-cycloheptene (906076-75-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/ol060530l

Reference yield:

((1R,2R)-5-Benzenesulfonyl-2-methyl-cyclohepta-3,5-dienyloxy)-tert-butyl-dimethyl-silane (606129-09-3) → (4R,5S,6S,7S)-1-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-cycloheptene (906076-75-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / 4-(3-phenylpropyl) pyridine N-oxide; NaOCl / Jacobsen's catalyst / CH₂Cl₂ / 19 h / 0 - 20 °C

2: 86 percent / ethanol / 6.5 h / 55 °C

3: 95 percent / toluene; tetrahydrofuran / 0.5 h / 20 °C

4: 97 percent / triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

With sodium hypochlorite; triethylamine; 4-(3-phenylpropyl)pyridine-N-oxide; Jacobsen's catalyst; In tetrahydrofuran; ethanol; dichloromethane; toluene; 2: Lawton addition;

DOI:10.1021/ol060530l

Reference yield:

tert-butyldimethyl(((1S,2R,3R,7S)-2-methyl-6-(phenylsulfonyl)-8-oxabicyclo[5.1.0]oct-5-en-3-yl)oxy)silane (906076-69-5) → (4R,5S,6S,7S)-1-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-cycloheptene (906076-75-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / ethanol / 6.5 h / 55 °C

2: 95 percent / toluene; tetrahydrofuran / 0.5 h / 20 °C

3: 97 percent / triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

With triethylamine; In tetrahydrofuran; ethanol; dichloromethane; toluene; 1: Lawton addition;

DOI:10.1021/ol060530l

upstream raw materials:

(1S,2S,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol

t-butyldimethylsiyl triflate

tert-butyldimethyl(((1S,2R,3R,7S)-2-methyl-6-(phenylsulfonyl)-8-oxabicyclo[5.1.0]oct-5-en-3-yl)oxy)silane

(1S,4R,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-4-(3,5-dimethyl-pyrazol-1-yl)-7-methyl-cyclohept-2-enol

Downstream raw materials:

(1R,5S,6S,7S)-6-(tert-butyldimethylsilyloxy)-5,7-dimethyl-4-(phenylsulfonyl)cyclohept-3-enol