(E)-(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hex-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hex-2-enoic acid methyl ester
• CAS No.: 145655-04-5
• Molecular Formula: C₂₅H₂₉NO₅
• Molecular Weight: 423.509
• Mol file: 145655-04-5.mol

Synonyms:(E)-(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hex-2-enoic acid methyl ester

Chemical Property of (E)-(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hex-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hex-2-enoic acid methyl ester

There total 1 articles about (E)-(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hex-2-enoic acid methyl ester 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: 98.0%

(E)-(4S,5S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-hydroxy-6-phenyl-hex-2-enoic acid methyl ester (145655-03-4) → (E)-(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hex-2-enoic acid methyl ester (145655-04-5)

Guidance literature:

With acetic anhydride; dimethyl sulfoxide; for 18h; Ambient temperature;

DOI:10.1016/S0040-4039(00)60888-2

Reference yield: 88.0%

(E)-(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hex-2-enoic acid methyl ester (145655-04-5) → (S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hexanoic acid methyl ester (145655-05-6)

Guidance literature:

With hydrogen; Pd-BaSO₄; In methanol; for 4h; under 760 Torr; Ambient temperature;

DOI:10.1016/S0040-4039(00)60888-2

Reference yield:

(E)-(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hex-2-enoic acid methyl ester (145655-04-5) → (3R,5S,1'S)-3-Benzyl-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one (145655-09-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / H₂ / Pd/BaSO₄ / methanol / 4 h / 760 Torr / Ambient temperature

2: NaBH₄ / methanol / 2 h / -50 °C

4: 40percent TFA in CH₂Cl₂ / 0.17 h / Ambient temperature

With sodium tetrahydroborate; hydrogen; trifluoroacetic acid; Pd-BaSO₄; In methanol;

DOI:10.1016/S0040-4039(00)60888-2

upstream raw materials:

(E)-(4S,5S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-hydroxy-6-phenyl-hex-2-enoic acid methyl ester

Downstream raw materials:

(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hexanoic acid methyl ester

(3R,5S,1'S)-3-Benzyl-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one

(3R,5S,1'S)-3-Benzyl-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one

(5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one