(4S)-4-benzyl-3-((2S,4R,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2,4,6-trimethylheptanoyl)-1,3-oxazolan-2-one

Base Information

• Chemical Name: (4S)-4-benzyl-3-((2S,4R,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2,4,6-trimethylheptanoyl)-1,3-oxazolan-2-one
• CAS No.: 1437124-38-3
• Molecular Formula: C₂₆H₄₃NO₄Si
• Molecular Weight: 461.717
• Mol file: 1437124-38-3.mol

Synonyms:(4S)-4-benzyl-3-((2S,4R,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2,4,6-trimethylheptanoyl)-1,3-oxazolan-2-one

Chemical Property of (4S)-4-benzyl-3-((2S,4R,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2,4,6-trimethylheptanoyl)-1,3-oxazolan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-benzyl-3-((2S,4R,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2,4,6-trimethylheptanoyl)-1,3-oxazolan-2-one

There total 5 articles about (4S)-4-benzyl-3-((2S,4R,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2,4,6-trimethylheptanoyl)-1,3-oxazolan-2-one 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%

(4S)-4-benzyl-3-((4S,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4,6-dimethylheptanoyl)-1,3-oxazolan-2-one (1437124-32-7) + methyl iodide (74-88-4) → (4S)-4-benzyl-3-((2S,4R,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2,4,6-trimethylheptanoyl)-1,3-oxazolan-2-one (1437124-38-3)

Guidance literature:

(4S)-4-benzyl-3-((4S,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4,6-dimethylheptanoyl)-1,3-oxazolan-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c3ra22754e

Reference yield:

ethyl (4R,6S)-7-(acetyloxy)-4,6-dimethyl-2-heptenoate → (4S)-4-benzyl-3-((2S,4R,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2,4,6-trimethylheptanoyl)-1,3-oxazolan-2-one (1437124-38-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / 0 - 25 °C / Inert atmosphere

2.1: potassium carbonate / ethanol / 12 h / 25 °C / Inert atmosphere

3.1: 1H-imidazole / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere

4.1: lithium hydroxide monohydrate / water; methanol / 2 h / 0 - 25 °C / Inert atmosphere

5.1: triethylamine; pivaloyl chloride; lithium chloride / tetrahydrofuran / 3 h / -20 - 0 °C / Inert atmosphere

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

6.2: 2 h / -78 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; nickel(II) chloride hexahydrate; lithium hydroxide monohydrate; sodium hexamethyldisilazane; pivaloyl chloride; potassium carbonate; triethylamine; lithium chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1039/c3ra22754e

Reference yield:

ethyl (4S,6S)-7-hydroxy-4,6-dimethylheptanoate (1437124-14-5) → (4S)-4-benzyl-3-((2S,4R,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2,4,6-trimethylheptanoyl)-1,3-oxazolan-2-one (1437124-38-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate / water; methanol / 2 h / 0 - 25 °C / Inert atmosphere

3.1: triethylamine; pivaloyl chloride; lithium chloride / tetrahydrofuran / 3 h / -20 - 0 °C / Inert atmosphere

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 °C / Inert atmosphere

With 1H-imidazole; lithium hydroxide monohydrate; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1039/c3ra22754e

upstream raw materials:

ethyl (4S,6S)-7-(acetyloxy)-4,6-dimethylheptanoate

(4S)-4-benzyl-3-((4S,6S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4,6-dimethylheptanoyl)-1,3-oxazolan-2-one

methyl iodide

ethyl (4S,6S)-7-hydroxy-4,6-dimethylheptanoate

Downstream raw materials:

(4S)-4-benzyl-3-[(4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one

(4S)-4-benzyl-3-[(2S,4S,6R,8S)-2,4,6,8-tetramethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one