(R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one

Base Information

• Chemical Name: (R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one
• CAS No.: 1379802-66-0
• Molecular Formula: C₃₁H₃₇NO₄Si
• Molecular Weight: 515.725
• Mol file: 1379802-66-0.mol

Synonyms:(R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one

Chemical Property of (R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one

There total 2 articles about (R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-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: 95.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (4R,2'R,3'S)-N-(3-hydroxy-2-methylbutanoyl)-4-benzyl-2-oxazolidinone (468756-88-9) → (R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one (1379802-66-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 44h; Inert atmosphere;

DOI:10.1002/chem.201102797

Reference yield:

(3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) → (R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one (1379802-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane; toluene / 0 - 8 °C / Inert atmosphere

1.2: -78 - 0 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 44 h / 20 °C / Inert atmosphere

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

DOI:10.1002/chem.201102797

Reference yield: 76.0%

(R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one (1379802-66-0) + benzyl alcohol (100-51-6,185532-71-2) → (2R,3S)-benzyl 3-(tert-butyldiphenylsilyloxy)-2-methylbutanoate (1379802-88-6)

Guidance literature:

benzyl alcohol; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h; Inert atmosphere;

(R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one; In tetrahydrofuran; hexane; at 0 ℃; for 1.75h; Inert atmosphere;

DOI:10.1002/chem.201102797

upstream raw materials:

(3R)-3-propionyl-4-benzyloxazolidin-2-one

tert-butylchlorodiphenylsilane

(4R,2'R,3'S)-N-(3-hydroxy-2-methylbutanoyl)-4-benzyl-2-oxazolidinone

Downstream raw materials:

(2S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal oxime

(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)-2-(trityloxy)ethanol

(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)ethane-1,2-diol

(R)-4-((1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-1-hydroxy-2,4-dimethyl-3-oxohexyl)-1,3-dioxolan-2-one