Isobutyric acid (1S,2S,3R,4R)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester

Base Information

• Chemical Name: Isobutyric acid (1S,2S,3R,4R)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester
• CAS No.: 473759-05-6
• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.455
• Mol file: 473759-05-6.mol

Synonyms:Isobutyric acid (1S,2S,3R,4R)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester

Chemical Property of Isobutyric acid (1S,2S,3R,4R)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Isobutyric acid (1S,2S,3R,4R)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester

There total 3 articles about Isobutyric acid (1S,2S,3R,4R)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl 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: 90.0%

Isobutyric acid (1S,2S,3S,4S)-1-(2-benzyloxy-ethyl)-3,5-dihydroxy-2,4-dimethyl-pentyl ester (473759-07-8) → Isobutyric acid (1S,2S,3R,4R)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester (473759-05-6)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; at 20 ℃; for 2h;

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

Reference yield:

(2S,4R,5S)-7-Benzyloxy-5-hydroxy-2,4-dimethyl-1-triisopropylsilanyloxy-heptan-3-one (213385-38-7) → Isobutyric acid (1S,2S,3R,4R)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester (473759-05-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / SmI₂ / tetrahydrofuran / 2.5 h / 0 °C

2: 91 percent / HF*pyridine / tetrahydrofuran / 7 h / 20 °C

3: 90 percent / TEMPO; PhI(OAc)2 / 2 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; samarium diiodide; [bis(acetoxy)iodo]benzene; pyridine hydrogenfluoride; In tetrahydrofuran; 1: Evans-Tishchenko reduction;

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

Reference yield:

Isobutyric acid (1S,2S,3S,4S)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-pentyl ester (473759-06-7) → Isobutyric acid (1S,2S,3R,4R)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester (473759-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / HF*pyridine / tetrahydrofuran / 7 h / 20 °C

2: 90 percent / TEMPO; PhI(OAc)2 / 2 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; pyridine hydrogenfluoride; In tetrahydrofuran;

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

upstream raw materials:

Isobutyric acid (1S,2S,3S,4S)-1-(2-benzyloxy-ethyl)-3,5-dihydroxy-2,4-dimethyl-pentyl ester

(2S,4R,5S)-7-Benzyloxy-5-hydroxy-2,4-dimethyl-1-triisopropylsilanyloxy-heptan-3-one

Isobutyric acid (1S,2S,3S,4S)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-pentyl ester

Downstream 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

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

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

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