[1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester
• CAS No.: 503186-55-8
• Molecular Formula: C₂₃H₃₇NO₄
• Molecular Weight: 391.551
• Mol file: 503186-55-8.mol

Synonyms:[1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester

Chemical Property of [1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester

There total 6 articles about [1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl 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: 27.0%

1,1-dimethylethyl <2-<4-(1,1-dimethylethoxy)-2,6-dimethylphenyl>-1(S)-formylethyl>carbamate (137650-17-0) + allylmagnesium bromide (1730-25-2) → [1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester (503186-56-9) + [1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester (503186-55-8)

Guidance literature:

1,1-dimethylethyl <2-<4-(1,1-dimethylethoxy)-2,6-dimethylphenyl>-1(S)-formylethyl>carbamate; allylmagnesium bromide; In tetrahydrofuran; diethyl ether; at 0 ℃; for 4h;

With Rochelle's salt; In methanol; hexane; water; toluene; at 20 ℃; for 1h;

Reference yield:

N-<(1,1-dimethylethoxy)carbonyl>-O-(1,1-dimethylethyl)-2,6-dimethyl-L-tyrosine methyl ester (137650-16-9) → [1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester (503186-55-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DIBAL-H / toluene; various solvent(s) / 1 h / -78 °C

1.2: Rochelle's salt / toluene; various solvent(s) / 1 h

2.1: 38 mg / tetrahydrofuran; diethyl ether / 4 h / 0 °C

With diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1021/jm025608s

Reference yield:

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoic acid → [1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester (503186-55-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride / 1.5 h

2.1: 71 percent / c. H₂SO₄ / CH₂Cl₂ / 258.58 Torr

3.1: NHMe₂ / tetrahydrofuran / 1 h

4.1: 302 mg / Et₃N / tetrahydrofuran / 1 h

5.1: DIBAL-H / toluene; various solvent(s) / 1 h / -78 °C

5.2: Rochelle's salt / toluene; various solvent(s) / 1 h

6.1: 38 mg / tetrahydrofuran; diethyl ether / 4 h / 0 °C

With thionyl chloride; sulfuric acid; diisobutylaluminium hydride; dimethyl amine; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jm025608s

upstream raw materials:

1,1-dimethylethyl <2-<4-(1,1-dimethylethoxy)-2,6-dimethylphenyl>-1(S)-formylethyl>carbamate

allylmagnesium bromide

N-<(1,1-dimethylethoxy)carbonyl>-O-(1,1-dimethylethyl)-2,6-dimethyl-L-tyrosine methyl ester

Fmoc-2,6-dimethyl-(L)-Tyr-OMe

Downstream raw materials:

2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-non-4-enoic acid

2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-dihydroxy-non-4-enoic acid

2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-non-4-enethioic acid S-benzyl ester