[(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane

Base Information

• Chemical Name: [(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane
• CAS No.: 327628-40-0
• Molecular Formula: C₃₁H₄₉BSi
• Molecular Weight: 460.627
• Mol file: 327628-40-0.mol

Synonyms:[(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane

Chemical Property of [(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane

There total 1 articles about [(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane 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:

allyldimethylphenylsilane (18001-18-8) + (-)-B-methoxydiisopinocampheylborane (85134-98-1) → [(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane (327628-40-0)

Guidance literature:

allyldimethylphenylsilane; With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; at -78 - -45 ℃;

(-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

DOI:10.1021/jo0511290

Reference yield: 83.0%

[(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane (327628-40-0) + (2S,3R)-2,3-dibenzyloxy-4-penten-1-al (535994-37-7) → (3R,4S,5S,6R)-5,6-dibenzyloxy-3-(dimethylphenylsilanyl)octa-1,7-dien-4-ol + (3S,4R,5S,6R)-5,6-dibenzyloxy-3-(dimethylphenylsilanyl)octa-1,7-dien-4-ol (538334-67-7)

Guidance literature:

[(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane; (2S,3R)-2,3-dibenzyloxy-4-penten-1-al; With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 - 23 ℃; for 16h;

With dihydrogen peroxide; In tetrahydrofuran; water; at 23 ℃; for 2h; pH=7; Title compound not separated from byproducts;

DOI:10.1021/ol034349d

Reference yield:

undecylaldehyde (112-44-7) + [(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane (327628-40-0) → (3R,4S)-3-(dimethylphenylsilanyl)-4-hydroxytridec-1-ene + (3S,4R)-3-(dimethylphenylsilanyl)-4-hydroxytridec-1-ene (863604-36-8)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1021/jo0511290

upstream raw materials:

allyldimethylphenylsilane

(-)-B-methoxydiisopinocampheylborane

Downstream raw materials:

(3S,4R,7S)-7-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-3-(dimethyl-phenyl-silanyl)-7-methyl-non-1-en-4-ol

(3S,4R)-3-dimethylphenylsilanyl-4-hydroxy-1,6-heptadiene

(3S,4R,5S,6R)-5,6-dibenzyloxy-3-(dimethylphenylsilanyl)octa-1,7-dien-4-ol

(2R,5S)-5-(benzyloxymethyl)-2-[(1R)-1-(hydroxy)undecyl]tetrahydrofuran

Refernces

• 1、 Tinsley, Jennifer M.,Roush, William R.. "Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes". . p. 10818 - 10819. Retrieved 2007/10/03.