(E)-(4S,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(4S,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester
• CAS No.: 127882-33-1
• Molecular Formula: C₁₉H₂₇NO₇S
• Molecular Weight: 413.492
• Mol file: 127882-33-1.mol

Synonyms:(E)-(4S,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester

Chemical Property of (E)-(4S,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-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)-(4S,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester

There total 4 articles about (E)-(4S,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-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: 100.0%

methyl (4S,5S,2E)-5-amino-N-<(tert-butyloxy)carbonyl>-4-hydroxy-6-phenyl-2-hexanoate (134210-24-5) + methanesulfonyl chloride (124-63-0) → (E)-(4S,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester (127882-33-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)60117-X

Reference yield:

(S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid (82042-48-6) → (E)-(4S,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester (127882-33-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent

2: 70 percent / m-chloroperbenzoic acid / CH₂Cl₂

3: 94 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: 100 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With tetrabutyl ammonium fluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)60117-X

Reference yield:

Methyl (S)-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoate (118457-05-9) → (E)-(4S,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester (127882-33-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / m-chloroperbenzoic acid / CH₂Cl₂

2: 94 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

3: 100 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With tetrabutyl ammonium fluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)60117-X

upstream raw materials:

methyl (4S,5S,2E)-5-amino-N-<(tert-butyloxy)carbonyl>-4-hydroxy-6-phenyl-2-hexanoate

methanesulfonyl chloride

Methyl (S)-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoate

(S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid

Downstream raw materials:

Methyl (S)-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoate

(E)-(2R,5S)-5-tert-Butoxycarbonylamino-2-tert-butyl-6-phenyl-hex-3-enoic acid methyl ester

(E)-(2S,5S)-5-tert-Butoxycarbonylamino-2-isopropyl-6-phenyl-hex-3-enoic acid methyl ester

(E)-(2S,5S)-5-tert-Butoxycarbonylamino-2-isobutyl-6-phenyl-hex-3-enoic acid methyl ester