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

Base Information

• Chemical Name: 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-dihydroxy-non-4-enoic acid
• CAS No.: 503186-63-8
• Molecular Formula: C₃₃H₄₇NO₇
• Molecular Weight: 569.739
• Mol file: 503186-63-8.mol

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

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

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-dihydroxy-non-4-enoic acid

There total 9 articles about 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-dihydroxy-non-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:

2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-dihydroxy-non-4-enethioic acid S-benzyl ester → 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-dihydroxy-non-4-enoic acid (503186-63-8)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 3h;

DOI:10.1021/jm025608s

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-dihydroxy-non-4-enoic acid (503186-63-8)

Guidance literature:

Multi-step reaction with 3 steps

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

2: Cl₂(PCy₃)(IMesH₂)RuCHPh / CH₂Cl₂ / 40 °C

3: 16 mg / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water;

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-dihydroxy-non-4-enoic acid (503186-63-8)

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 / 40 °C

4.1: 16 mg / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium hydroxide; dihydrogen peroxide; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;

DOI:10.1021/jm025608s

upstream raw materials:

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

2-benzyl-3-hydroxy-pent-4-enethioic acid S-benzyl ester

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