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

Base Information

• Chemical Name: (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid
• CAS No.: 82042-48-6
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• Mol file: 82042-48-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid 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: 82.0%

(S)-2-t-butoxycarbonylamino-1-phenyl-6-trimethylsilylhex-E/Z-3-en-5-yne → (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid (82042-48-6)

Guidance literature:

(S)-2-t-butoxycarbonylamino-1-phenyl-6-trimethylsilylhex-E/Z-3-en-5-yne; With borane; cyclohexene;

With dihydrogen peroxide;

DOI:10.1021/ja0551382

Reference yield: 75.0%

(S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexen-1-ol (155099-11-9) → (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid (82042-48-6)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; for 1h;

DOI:10.1016/0040-4039(96)01108-2

Reference yield:

Boc-Phe-OH N,O-dimethyl hydroxamate (87694-53-9) → (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid (82042-48-6)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₂O / 3 h / -15 °C

2: NaBH₄ / methanol / 1 h / -20 - 0 °C

3: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: 50 percent Chromat_. / KOtBu / tetrahydrofuran / Ambient temperature; variation of base and temperature

5: 1.) 9-BBN, 2.) NaOH, H₂O₂ / 1.) THF, RT, 6 h, 2.) 60 deg C, 1 h

6: 75 percent / 2M Jones reagent / acetone / 1 h / 0 °C

With sodium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; jones reagent; diethyl ether; potassium tert-butylate; dihydrogen peroxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1016/0040-4039(96)01108-2

upstream raw materials:

(Z)-(S)-<1-(phenylmethyl)-5-(trimethylsilyl)-3-hexen-5-ynyl>carbamic acid 1,1-dimethylethyl ester

Boc-L-phenylalaninal

(S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexen-1-ol

Boc-Phe-OH N,O-dimethyl hydroxamate

Downstream raw materials:

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

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

Methyl (3R,4R,5S)-5-<(tert-butoxycarbonyl)amino>-3,4-epoxy-6-phenylhexanoate

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