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

Base Information

• Chemical Name: (S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hexanoic acid methyl ester
• CAS No.: 145655-05-6
• Molecular Formula: C₂₅H₃₁NO₅
• Molecular Weight: 425.525
• Mol file: 145655-05-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hexanoic 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: 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)-(4S,5S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-hydroxy-6-phenyl-hex-2-enoic acid methyl ester (145655-03-4) → (S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hexanoic acid methyl ester (145655-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Ac₂O/DMSO / 18 h / Ambient temperature

2: 88 percent / H₂ / Pd/BaSO₄ / methanol / 4 h / 760 Torr / Ambient temperature

With hydrogen; acetic anhydride; dimethyl sulfoxide; Pd-BaSO₄; In methanol;

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

Reference yield:

(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hexanoic acid methyl ester (145655-05-6) → (5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one (145655-07-8) + Benzyl-[(S)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (145655-12-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -50 ℃; for 2h; Yield given. Yields of byproduct given;

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

upstream raw materials:

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

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

Downstream raw materials:

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

Benzyl-[(S)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl 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