<2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide

Base Information

• Chemical Name: <2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide
• CAS No.: 157220-45-6
• Molecular Formula: C₂₀H₃₅NO₄Si
• Molecular Weight: 381.588
• Mol file: 157220-45-6.mol

Synonyms:<2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide

Chemical Property of <2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide

There total 4 articles about <2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide 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: 100.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3S)-4-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylbutanamide (162255-08-5) → <2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide (157220-45-6)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 25 ℃; for 16h;

DOI:10.1021/ja00117a014

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → <2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide (157220-45-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) dibutylboron triflate, triethylamine / 1.) CH₂Cl₂, 0 deg C, 2.) CH₂Cl₂, -78 -> 0 deg C

2: 99 percent / trimethylaluminum / tetrahydrofuran; toluene; CH₂Cl₂ / 1.5 h / 0 °C

3: 100 percent / imidazole / dimethylformamide / 5.5 h / 23 °C

With 1H-imidazole; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9606113

Reference yield:

(4S,5R)-3-((2S,3S)-4-Benzyloxy-3-hydroxy-2-methyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one (157318-10-0) → <2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide (157220-45-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / trimethylaluminum / tetrahydrofuran; toluene; CH₂Cl₂ / 1.5 h / 0 °C

2: 100 percent / imidazole / dimethylformamide / 5.5 h / 23 °C

With 1H-imidazole; trimethylaluminum; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9606113

upstream raw materials:

tert-butyldimethylsilyl chloride

(2S,3S)-4-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylbutanamide

benzyloxyacetoaldehyde

(4S,5R)-3-((2S,3S)-4-Benzyloxy-3-hydroxy-2-methyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one

Downstream raw materials:

(E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol

<2S,3S>-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-4-(phenylmethoxy)butanal

(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol

(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde