(R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane

Base Information

• Chemical Name: (R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane
• CAS No.: 872359-75-6
• Molecular Formula: C₂₅H₄₁BOSi₂
• Molecular Weight: 424.582
• Mol file: 872359-75-6.mol

Synonyms:(R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane

Chemical Property of (R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane

There total 2 articles about (R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane 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:

trimethyl(prop-1-ynyl)silane (6224-91-5) → (R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane (872359-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert-butyllithium / tetrahydrofuran; pentane / 1 h / 0 °C

1.2: diethyl ether; tetrahydrofuran; pentane / 0.5 h / -78 °C

1.3: trimethylsilyl triflate / diethyl ether; tetrahydrofuran; pentane / -78 - 20 °C

2.1: 1.23 g / tetrahydrofuran / 3 h / -78 °C

With tert.-butyl lithium; In tetrahydrofuran; pentane;

DOI:10.1021/ol051886k

Reference yield:

(R)-10-Trimethylsilanyl-9-(3-trimethylsilanyl-prop-2-ynyl)-9-bora-bicyclo[3.3.2]decane (872359-59-6) + benzaldehyde (100-52-7) → (R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane (872359-75-6)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1021/ol051886k

Reference yield:

(R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane (872359-75-6) + pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) → 9-(1S,2S-pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane (848618-13-3) + (-)-(1S)-1-phenyl-2-(trimethylsilyl)-2,3-butadien-1-ol (872420-37-6)

Guidance literature:

In acetonitrile; at 81 ℃; for 15h;

DOI:10.1021/ol051886k

upstream raw materials:

(R)-10-Trimethylsilanyl-9-(3-trimethylsilanyl-prop-2-ynyl)-9-bora-bicyclo[3.3.2]decane

benzaldehyde

trimethyl(prop-1-ynyl)silane

Downstream raw materials:

9-(1S,2S-pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane

(-)-(1S)-1-phenyl-2-(trimethylsilyl)-2,3-butadien-1-ol