Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodeca-5,11-dienyl ester

Base Information

• Chemical Name: Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodeca-5,11-dienyl ester
• CAS No.: 473759-10-3
• Molecular Formula: C₃₇H₆₁NO₇Si
• Molecular Weight: 659.979
• Mol file: 473759-10-3.mol

Synonyms:Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodeca-5,11-dienyl ester

Chemical Property of Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodeca-5,11-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodeca-5,11-dienyl ester

There total 14 articles about Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodeca-5,11-dienyl 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: 60.0%

Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-2,4,8,10-tetramethyl-7-oxo-3,9-bis-triethylsilanyloxy-dodeca-5,11-dienyl ester (473759-09-0) → Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodeca-5,11-dienyl ester (473759-10-3)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 40 ℃; for 4h;

DOI:10.1016/S0040-4039(02)01217-0

Reference yield:

triethylsilyl chloride (994-30-9) → Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodeca-5,11-dienyl ester (473759-10-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / imidazole / dimethylformamide / 2 h / 20 °C

2: 60 percent / AcOH; H₂O / tetrahydrofuran / 4 h / 40 °C

With 1H-imidazole; water; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)01217-0

Reference yield:

N-((Z)-(3R,4R,5R)-3,5-Dimethyl-6-oxo-4-triethylsilanyloxy-hex-1-enyl)-N-methyl-formamide (473759-03-4) → Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodeca-5,11-dienyl ester (473759-10-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / n-BuLi / tetrahydrofuran / 4 h / -78 °C

2: 81 percent / TPAP; NMO / CH₂Cl₂ / 1 h / 20 °C

3: 52 percent / LiCl; DBU / tetrahydrofuran; acetonitrile / 3 h / 20 °C

4: 87 percent / imidazole / dimethylformamide / 2 h / 20 °C

5: 60 percent / AcOH; H₂O / tetrahydrofuran / 4 h / 40 °C

With 1H-imidazole; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; water; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3: Horner-Wadsworth-Emmons coupling;

DOI:10.1016/S0040-4039(02)01217-0

upstream raw materials:

Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-2,4,8,10-tetramethyl-7-oxo-3,9-bis-triethylsilanyloxy-dodeca-5,11-dienyl ester

triethylsilyl chloride

N-((Z)-(3R,4R,5R)-3,5-Dimethyl-6-oxo-4-triethylsilanyloxy-hex-1-enyl)-N-methyl-formamide

N-((Z)-(3R,4R,5S)-6-Hydroxy-3,5-dimethyl-4-triethylsilanyloxy-hex-1-enyl)-N-methyl-formamide

Downstream raw materials:

Isobutyric acid (Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodec-11-enyl ester