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

Base Information

• Chemical Name: 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
• CAS No.: 503186-65-0
• Molecular Formula: C₅₂H₈₁NO₆SSi₂
• Molecular Weight: 904.455
• Mol file: 503186-65-0.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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:

1,1-dimethylethyl <2-<4-(1,1-dimethylethoxy)-2,6-dimethylphenyl>-1(S)-formylethyl>carbamate (137650-17-0) → 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 (503186-65-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 38 mg / tetrahydrofuran; diethyl ether / 4 h / 0 °C

2: Cl₂(PCy₃)(IMesH₂)RuCHPh / CH₂Cl₂ / 2 h / 45 °C

3: imidazole / dimethylformamide / 16 h

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm025608s

Reference yield:

N-<(1,1-dimethylethoxy)carbonyl>-O-(1,1-dimethylethyl)-2,6-dimethyl-L-tyrosine methyl ester (137650-16-9) → 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 (503186-65-0)

Guidance literature:

Multi-step reaction with 4 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

3.1: Cl₂(PCy₃)(IMesH₂)RuCHPh / CH₂Cl₂ / 2 h / 45 °C

4.1: imidazole / dimethylformamide / 16 h

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm025608s

Reference yield:

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoic 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 (503186-65-0)

Guidance literature:

Multi-step reaction with 8 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

7.1: Cl₂(PCy₃)(IMesH₂)RuCHPh / CH₂Cl₂ / 2 h / 45 °C

8.1: imidazole / dimethylformamide / 16 h

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; thionyl chloride; sulfuric acid; diisobutylaluminium hydride; dimethyl amine; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm025608s

upstream raw materials:

tert-butyldimethylsilyl chloride

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

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

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

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