(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Base Information

• Chemical Name: (2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide
• CAS No.: 175979-70-1
• Molecular Formula: C₂₂H₃₉NO₃Si
• Molecular Weight: 393.642

Synonyms:(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Chemical Property of (2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

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Technology Process of (2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

There total 2 articles about (2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 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:

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3) + (R)-tert-butyl-(2-iodo-1-methyl-ethoxy)-dimethyl-silane → (2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (175979-70-1)

Guidance literature:

With lithium chloride; lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, -78 -> 23 deg C, 2.) THF, 45 deg C, 14 h;

DOI:10.1021/jo952032o

Reference yield:

2-(tert-butyldimethylsilyloxy)propyl iodide (113401-50-6) + N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3) → (2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (175979-70-1) + (2R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (176198-62-2)

Guidance literature:

With lithium chloride; lithium diisopropyl amide; Multistep reaction; 1.) THF, -78 -> 23 deg C, 2.) THF, 45 deg C, 14 h;

DOI:10.1021/jo952032o

Reference yield: 92.0%

(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (175979-70-1) → (2R,4R)-4-Hydroxy-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (176198-66-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.25h;

DOI:10.1021/jo952032o

upstream raw materials:

2-(tert-butyldimethylsilyloxy)propyl iodide

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide

Downstream raw materials:

(2R,4R)-4-Hydroxy-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

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