(S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal

Base Information

• Chemical Name: (S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal
• CAS No.: 412912-89-1
• Molecular Formula: C₁₅H₂₄O₂Si
• Molecular Weight: 264.44
• Mol file: 412912-89-1.mol

Synonyms:(S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal

Chemical Property of (S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal

There total 11 articles about (S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal 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: 52.0%

(S)-3-((tert-butyldimethylsilyl)oxy)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-phenylpropan-1-one → (S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal (412912-89-1)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at 0 ℃; for 2h;

DOI:10.1002/anie.201403118

Reference yield:

ethyl (S)-(-)-3-(tert-butyldimethylsilyloxy)-3-phenylpropanoate (112635-77-5) → (S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal (412912-89-1)

Guidance literature:

ethyl (S)-(-)-3-(tert-butyldimethylsilyloxy)-3-phenylpropanoate; With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h; Inert atmosphere;

With Rochelle's salt; In dichloromethane; water; toluene;

DOI:10.1016/j.tetasy.2013.01.005

Reference yield:

tert-butyldimethylsilyl vinyl ether (66031-93-4) + benzaldehyde (100-52-7) → (S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal (412912-89-1) + (R)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal

Guidance literature:

benzaldehyde; With C₁₀₆H₇₃F₆N₃O₈P₂S₂; In chloroform; at -60 ℃; for 0.25h; Inert atmosphere; Schlenk technique;

tert-butyldimethylsilyl vinyl ether; In chloroform; at -60 ℃; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.1c07447

upstream raw materials:

tert-butyl-dimethyl-(1-phenyl-but-3-enyloxy)-silane

(S)-1-Phenyl-3-buten-1-ol

benzaldehyde

tert-butyldimethylsilyl chloride

Downstream raw materials:

(4S,6S)-6-(tert-butyldimethylsilyl)oxy-4-hydroxy-6-phenyl-1-hexene

(4R,6S)-6-(tert-butyldimethylsilyl)oxy-4-hydroxy-6-phenyl-1-hexene

(1S,3S)-1-phenylhex-5-ene-1,3-diol

5-epi-diospongin A