ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3S,4S,5S)-tetrahydro-2-furancarboxylate

Base Information

• Chemical Name: ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3S,4S,5S)-tetrahydro-2-furancarboxylate
• CAS No.: 869733-29-9
• Molecular Formula: C₂₅H₄₄O₅Si₂
• Molecular Weight: 480.792
• Mol file: 869733-29-9.mol

Synonyms:ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3S,4S,5S)-tetrahydro-2-furancarboxylate

Chemical Property of ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3S,4S,5S)-tetrahydro-2-furancarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3S,4S,5S)-tetrahydro-2-furancarboxylate

There total 1 articles about ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3S,4S,5S)-tetrahydro-2-furancarboxylate 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%

tert-butyldimethylsilyl chloride (18162-48-6) + ethyl 3,4-dihydroxy-5-phenyl-(2S,3R,4R,5S)-tetrahydro-2-furancarboxylate (607376-08-9) → ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3S,4S,5S)-tetrahydro-2-furancarboxylate (869733-29-9)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2005.08.047

Reference yield:

ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3S,4S,5S)-tetrahydro-2-furancarboxylate (869733-29-9) → (2S,3S,4S,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan-2-carbaldehyde

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃;

DOI:10.1016/j.tetasy.2005.08.047

Reference yield:

ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3S,4S,5S)-tetrahydro-2-furancarboxylate (869733-29-9) → (-)-goniothales diol

Guidance literature:

Multi-step reaction with 4 steps

1.1: DIBAL-H / CH₂Cl₂; hexane / -78 °C

2.1: methanol / 20 °C

3.1: 94 percent / hydrogen; formic acid / palladium on carbon / methanol / 3 h / 20 °C

4.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4.2: 74 percent / Amberlyst 15 / methanol / 3 h

With formic acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; 2.1: Wittig olefination;

DOI:10.1016/j.tetasy.2005.08.047

upstream raw materials:

tert-butyldimethylsilyl chloride

ethyl 3,4-dihydroxy-5-phenyl-(2S,3R,4R,5S)-tetrahydro-2-furancarboxylate

Downstream raw materials:

methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2R,3S,4S,5S)-tetrahydro-2-furanyl]-(Z)-2-propenoate

methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2R,3S,4S,5S)-tetrahydro-2-furanyl]-propanoate

(-) Altholactone