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

Base Information

Chemical Name:2-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyl)-3-phenethyl-pent-4-enoic acid
CAS No.:749927-01-3
Molecular Formula:C₂₄H₃₉NO₄Si
Molecular Weight:433.663
Hs Code.:

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

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

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

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

There total 10 articles about 2-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyl)-3-phenethyl-pent-4-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: 86.0%

: 749927-00-2
tert-butoxycarbonylamino-acetic acid 1-(tert-butyl-dimethyl-silanyl)-5-phenyl-pent-2-enyl ester

: 749927-01-3
2-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyl)-3-phenethyl-pent-4-enoic acid

Guidance literature:: With lithium diisopropyl amide; zinc(II) chloride; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/j.tetlet.2004.05.157

Reference yield:

: 104-53-0
3-phenyl-propionaldehyde

: 749927-01-3
2-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyl)-3-phenethyl-pent-4-enoic acid

Guidance literature:: Multi-step reaction with 4 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

4: 86 percent / LDA / ZnCl₂ / tetrahydrofuran / -78 - 20 °C

With dmap; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; B-chlorodiisopinocampheylborane; lithium diisopropyl amide; zinc(II) chloride; In tetrahydrofuran; dichloromethane; 1: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tetlet.2004.05.157

Reference yield:

: 75553-23-0
(E)-5-phenyl-2-penten-1-ol

: 749927-01-3
2-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyl)-3-phenethyl-pent-4-enoic acid

Guidance literature:: Multi-step reaction with 6 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

6: 86 percent / LDA / ZnCl₂ / tetrahydrofuran / -78 - 20 °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; lithium diisopropyl amide; zinc(II) chloride; In tetrahydrofuran; dichloromethane; acetone; 2: reverse-Brook rearrangement / 3: Jones oxidation;
DOI:10.1016/j.tetlet.2004.05.157