(4S,5S)-trans-N-<(tert-butyloxy)carbonyl>-5-amino-4-hydroxy-6-phenylhex-2-enoic acid

Base Information

• Chemical Name: (4S,5S)-trans-N-<(tert-butyloxy)carbonyl>-5-amino-4-hydroxy-6-phenylhex-2-enoic acid
• CAS No.: 99113-32-3
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373
• Mol file: 99113-32-3.mol

Synonyms:(4S,5S)-trans-N-<(tert-butyloxy)carbonyl>-5-amino-4-hydroxy-6-phenylhex-2-enoic acid

Chemical Property of (4S,5S)-trans-N-<(tert-butyloxy)carbonyl>-5-amino-4-hydroxy-6-phenylhex-2-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-trans-N-<(tert-butyloxy)carbonyl>-5-amino-4-hydroxy-6-phenylhex-2-enoic acid

There total 5 articles about (4S,5S)-trans-N-<(tert-butyloxy)carbonyl>-5-amino-4-hydroxy-6-phenylhex-2-enoic 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:

[3-((S)-1-tert-Butoxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic acid methyl ester (124266-92-8,124339-16-8) → (2E,4R,S,5S)-5-<<(1,1-dimethylethoxy)carbonyl>amino>-4-hydroxy-6-phenyl-2-hexenoic acid (99113-32-3,99113-34-5,118386-98-4)

Guidance literature:

With sodium hydroxide; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jm00164a058

Reference yield:

Methyl (S)-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoate (118457-05-9) → (2E,4R,S,5S)-5-<<(1,1-dimethylethoxy)carbonyl>amino>-4-hydroxy-6-phenyl-2-hexenoic acid (99113-32-3,99113-34-5,118386-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 72 h / Ambient temperature

2: 1.1 g / 1 N NaOH / methanol / 2 h / Ambient temperature

With sodium hydroxide; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1021/jm00164a058

Reference yield:

Boc-L-phenylalaninal (72155-45-4) → (2E,4R,S,5S)-5-<<(1,1-dimethylethoxy)carbonyl>amino>-4-hydroxy-6-phenyl-2-hexenoic acid (99113-32-3,99113-34-5,118386-98-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1.) THF, hexane, -80 deg C, 1 h, 2.) a) -80 deg C, 1 h, b) room temp.

2: 1.) (cyclohexyl)2BH, 2.) 2 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) MeOH, room temp., 1 h

3: 64 percent / 1,1'-carbonyldiimidazole (CDI) / tetrahydrofuran / 3 h

4: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 72 h / Ambient temperature

5: 1.1 g / 1 N NaOH / methanol / 2 h / Ambient temperature

With sodium hydroxide; n-butyllithium; bis(cyclohexanyl)borane; dihydrogen peroxide; 3-chloro-benzenecarboperoxoic acid; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00164a058

upstream raw materials:

[3-((S)-1-tert-Butoxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic acid methyl ester

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

Boc-L-phenylalaninal

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

Downstream raw materials:

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

Boc-PheΨGly-ACHPA-Leu-NHCH2-m-Ph-CH2NH2

Boc-PheΨSta-Leu-NHCH2Ph

Boc-PheΨGly-ACHPA-Leu-NHCH2Ph