tert-butoxycarbonylamino-acetic acid 1-(tert-butyl-dimethyl-silanyl)-5-phenyl-pent-2-enyl ester

Base Information

• Chemical Name: tert-butoxycarbonylamino-acetic acid 1-(tert-butyl-dimethyl-silanyl)-5-phenyl-pent-2-enyl ester
• CAS No.: 749927-00-2
• Molecular Formula: C₂₄H₃₉NO₄Si
• Molecular Weight: 433.663
• Mol file: 749927-00-2.mol

Synonyms:tert-butoxycarbonylamino-acetic acid 1-(tert-butyl-dimethyl-silanyl)-5-phenyl-pent-2-enyl ester

Chemical Property of tert-butoxycarbonylamino-acetic acid 1-(tert-butyl-dimethyl-silanyl)-5-phenyl-pent-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butoxycarbonylamino-acetic acid 1-(tert-butyl-dimethyl-silanyl)-5-phenyl-pent-2-enyl ester

There total 8 articles about tert-butoxycarbonylamino-acetic acid 1-(tert-butyl-dimethyl-silanyl)-5-phenyl-pent-2-enyl 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:

BOC-glycine (4530-20-5) + (E)-(S)-1-(tert-Butyl-dimethyl-silanyl)-5-phenyl-pent-2-en-1-ol (749927-12-6) → tert-butoxycarbonylamino-acetic acid 1-(tert-butyl-dimethyl-silanyl)-5-phenyl-pent-2-enyl ester (749927-00-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/j.tetlet.2004.05.157

Reference yield:

3-phenyl-propionaldehyde (104-53-0) → tert-butoxycarbonylamino-acetic acid 1-(tert-butyl-dimethyl-silanyl)-5-phenyl-pent-2-enyl ester (749927-00-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / NaH / tetrahydrofuran / 1 h / 0 °C

2: (+)-DIP-Cl / tetrahydrofuran / 2 h / Heating

3: EDCI; DMAP / CH₂Cl₂ / 2 h / 0 °C

With dmap; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; B-chlorodiisopinocampheylborane; In tetrahydrofuran; dichloromethane; 1: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tetlet.2004.05.157

Reference yield:

(E)-5-phenyl-2-penten-1-ol (75553-23-0) → tert-butoxycarbonylamino-acetic acid 1-(tert-butyl-dimethyl-silanyl)-5-phenyl-pent-2-enyl ester (749927-00-2)

Guidance literature:

Multi-step reaction with 5 steps

1: imidazole / CH₂Cl₂ / 1 h / -78 - 20 °C

2: 80 percent / sec-BuLi; TMEDA / tetrahydrofuran / 1 h / -78 - 20 °C

3: 100 percent / H₂SO₄; CrO₃ / acetone

4: (+)-DIP-Cl / tetrahydrofuran / 2 h / Heating

5: EDCI; DMAP / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; chromium(VI) oxide; dmap; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; sec.-butyllithium; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; B-chlorodiisopinocampheylborane; In tetrahydrofuran; dichloromethane; acetone; 2: reverse-Brook rearrangement / 3: Jones oxidation;

DOI:10.1016/j.tetlet.2004.05.157

upstream raw materials:

BOC-glycine

(E)-(S)-1-(tert-Butyl-dimethyl-silanyl)-5-phenyl-pent-2-en-1-ol

3-phenyl-propionaldehyde

(E)-5-phenyl-2-penten-1-ol

Downstream raw materials:

(2S,3R)-2-tert-Butoxycarbonylamino-3-phenethyl-pent-4-enoic acid methyl ester

(2S,3R)-2-Amino-3-phenethyl-pent-4-enoic acid

2-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyl)-3-phenethyl-pent-4-enoic acid