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

Base Information

• Chemical Name: (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexen-1-ol
• CAS No.: 155099-11-9
• Molecular Formula: C₁₇H₂₅NO₃
• Molecular Weight: 291.39
• Mol file: 155099-11-9.mol

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

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

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-hexen-1-ol

There total 6 articles about (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexen-1-ol 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:

(S)-1-Benzyl-N-(tert-butoxycarbonyl)-5-<(tert-butyldimethylsilyl)oxy>-2-pentenylamine → (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(Z)-3-hexen-1-ol + (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexen-1-ol (155099-11-9)

Guidance literature:

With hydrogen fluoride; In acetonitrile; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00084a037

Reference yield:

Boc-Phe-OH N,O-dimethyl hydroxamate (87694-53-9) → (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexen-1-ol (155099-11-9)

Guidance literature:

Multi-step reaction with 5 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

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

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

Reference yield:

tert-butyl (1S)-1-benzyl-2-hydroxypent-4-enylcarbamate (1034089-11-6) → (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexen-1-ol (155099-11-9)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 50 percent Chromat_. / KOtBu / tetrahydrofuran / Ambient temperature; variation of base and temperature

3: 1.) 9-BBN, 2.) NaOH, H₂O₂ / 1.) THF, RT, 6 h, 2.) 60 deg C, 1 h

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; potassium tert-butylate; dihydrogen peroxide; triethylamine; In tetrahydrofuran; dichloromethane;

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

upstream raw materials:

(1S,2E)-(1-benzyl-penta-2,4-dienyl)-carbamic acid tert-butyl ester

Boc-Phe-OH N,O-dimethyl hydroxamate

tert-butyl (1S)-1-benzyl-2-hydroxypent-4-enylcarbamate

(S)-tert-butyl 3-oxo-1-phenylhex-5-en-2-ylcarbamate

Downstream raw materials:

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

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

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

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