tert-Butyl-((2S,4S)-6,6-dibromo-2,4-dimethyl-hex-5-enyloxy)-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-((2S,4S)-6,6-dibromo-2,4-dimethyl-hex-5-enyloxy)-diphenyl-silane
• CAS No.: 328114-44-9
• Molecular Formula: C₂₄H₃₂Br₂OSi
• Molecular Weight: 524.411
• Mol file: 328114-44-9.mol

Synonyms:tert-Butyl-((2S,4S)-6,6-dibromo-2,4-dimethyl-hex-5-enyloxy)-diphenyl-silane

Chemical Property of tert-Butyl-((2S,4S)-6,6-dibromo-2,4-dimethyl-hex-5-enyloxy)-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-((2S,4S)-6,6-dibromo-2,4-dimethyl-hex-5-enyloxy)-diphenyl-silane

There total 4 articles about tert-Butyl-((2S,4S)-6,6-dibromo-2,4-dimethyl-hex-5-enyloxy)-diphenyl-silane 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:

(2R,3R,5S)-6-(tert-butyldiphenylsilyloxy)-2,3-epoxy-5-methylhexan-1-ol (136374-58-8) → tert-Butyl-((2S,4S)-6,6-dibromo-2,4-dimethyl-hex-5-enyloxy)-diphenyl-silane (328114-44-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / Et₃N / CH₂Cl₂

2: BF₃*OEt₂ / CH₂Cl₂ / -78 °C

3: BCl₃ / methanol; CH₂Cl₂ / -78 °C

4: aq. NaIO₄ / tetrahydrofuran

5: Ph₃P / CH₂Cl₂

With sodium periodate; boron trifluoride diethyl etherate; boron trichloride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja005644l

Reference yield:

(2S,3S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexane-1,2-diol (328114-42-7) → tert-Butyl-((2S,4S)-6,6-dibromo-2,4-dimethyl-hex-5-enyloxy)-diphenyl-silane (328114-44-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaIO₄ / tetrahydrofuran

2: Ph₃P / CH₂Cl₂

With sodium periodate; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja005644l

Reference yield:

tert-Butyl-[(S)-2-methyl-3-((2R,3R)-3-trityloxymethyl-oxiranyl)-propoxy]-diphenyl-silane (328114-41-6) → tert-Butyl-((2S,4S)-6,6-dibromo-2,4-dimethyl-hex-5-enyloxy)-diphenyl-silane (328114-44-9)

Guidance literature:

Multi-step reaction with 4 steps

1: BF₃*OEt₂ / CH₂Cl₂ / -78 °C

2: BCl₃ / methanol; CH₂Cl₂ / -78 °C

3: aq. NaIO₄ / tetrahydrofuran

4: Ph₃P / CH₂Cl₂

With sodium periodate; boron trifluoride diethyl etherate; boron trichloride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja005644l

upstream raw materials:

carbon tetrabromide

(2R,3R,5S)-6-(tert-butyldiphenylsilyloxy)-2,3-epoxy-5-methylhexan-1-ol

(2S,3S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexane-1,2-diol

tert-Butyl-[(S)-2-methyl-3-((2R,3R)-3-trityloxymethyl-oxiranyl)-propoxy]-diphenyl-silane

Downstream raw materials:

(2S,4S)-1-(tert-butyldiphenylsiloxy)-6-iodo-2,4-dimethyl-5-(E)-heptene