(4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate

Base Information

• Chemical Name: (4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate
• CAS No.: 911033-98-2
• Molecular Formula: C₂₂H₃₂F₃NO₆Si
• Molecular Weight: 491.58
• Mol file: 911033-98-2.mol

Synonyms:(4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate

Chemical Property of (4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate

There total 3 articles about (4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate 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: 92.0%

(trifluoromethyl)trimethylsilane (81290-20-2) + 4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester (23632-68-0) → (4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate (911033-98-2)

Guidance literature:

With cesium fluoride; In tetrahydrofuran; at 20 ℃; for 2h; sonication;

DOI:10.1016/j.tet.2006.06.052

Reference yield:

N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) → (4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate (911033-98-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / p-TsOH*H₂O / toluene / 1.67 h / Heating

2: 45 percent / DMAP; ECD*HCl; Et₃N / tetrahydrofuran / 16 h / 20 °C

3: 92 percent / cesium fluoride / tetrahydrofuran / 2 h / 20 °C / sonication

With dmap; ECD*HCl; toluene-4-sulfonic acid; triethylamine; cesium fluoride; In tetrahydrofuran; toluene;

DOI:10.1016/j.tet.2006.06.052

Reference yield:

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid (23632-67-9) → (4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate (911033-98-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / DMAP; ECD*HCl; Et₃N / tetrahydrofuran / 16 h / 20 °C

2: 92 percent / cesium fluoride / tetrahydrofuran / 2 h / 20 °C / sonication

With dmap; ECD*HCl; triethylamine; cesium fluoride; In tetrahydrofuran;

DOI:10.1016/j.tet.2006.06.052

upstream raw materials:

(trifluoromethyl)trimethylsilane

4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester

N-benzyloxycarbonyl-L-glutamic acid

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid

Downstream raw materials:

(4S)-tert-butyl 4-(benzyloxycarbonyl)amino-6,6,6-trifluoro-5-hydroxyhexanoate

(4S,5R)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-hydroxyoxazolidine-3-carboxylate

(S)-4-[N-(benzyloxycarbonyl)-L-alanyl-L-valyl-L-leucyl]amino-6,6,6-trifluoro-5-oxohexanoic acid

(S)-4-[N-(benzyloxycarbonyl)-L-phenylalanyl-L-alanyl]amino-6,6,6-trifluoro-5-oxohexanoic acid