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

Base Information

• Chemical Name: (4S)-tert-butyl 4-(benzyloxycarbonyl)amino-6,6,6-trifluoro-5-hydroxyhexanoate
• CAS No.: 911034-02-1
• Molecular Formula: C₁₈H₂₄F₃NO₅
• Molecular Weight: 391.387
• Mol file: 911034-02-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (4S)-tert-butyl 4-(benzyloxycarbonyl)amino-6,6,6-trifluoro-5-hydroxyhexanoate 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: 69.0%

(4S,5R)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-hydroxyoxazolidine-3-carboxylate (911034-00-9) → (4S)-tert-butyl 4-(benzyloxycarbonyl)amino-6,6,6-trifluoro-5-hydroxyhexanoate (911034-02-1)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 23h;

DOI:10.1016/j.tet.2006.06.052

Reference yield: 68.0%

(4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate (911033-98-2) → (4S)-tert-butyl 4-(benzyloxycarbonyl)amino-6,6,6-trifluoro-5-hydroxyhexanoate (911034-02-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 16h;

DOI:10.1016/j.tet.2006.06.052

Reference yield:

N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) → (4S)-tert-butyl 4-(benzyloxycarbonyl)amino-6,6,6-trifluoro-5-hydroxyhexanoate (911034-02-1)

Guidance literature:

Multi-step reaction with 4 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

4: 68 percent / NaBH₄ / methanol / 16 h / 20 °C

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

DOI:10.1016/j.tet.2006.06.052

upstream raw materials:

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

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

N-benzyloxycarbonyl-L-glutamic acid

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

Downstream raw materials:

(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

(S)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-6,6,6-trifluoro-5-hydroxy-hexanoic acid tert-butyl ester

(S)-tert-butyl 4-[N-(benzyloxycarbonyl)-L-alanyl]amino-6,6,6-trifluoro-5-oxohexanoate