(S)-8-benzyl-3-[(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylbutanoyl]oxazolidin-2-one

Base Information

• Chemical Name: (S)-8-benzyl-3-[(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylbutanoyl]oxazolidin-2-one
• CAS No.: 101711-80-2
• Molecular Formula: C₂₁H₃₃NO₄Si
• Molecular Weight: 391.583
• Mol file: 101711-80-2.mol

Synonyms:(S)-8-benzyl-3-[(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylbutanoyl]oxazolidin-2-one

Chemical Property of (S)-8-benzyl-3-[(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylbutanoyl]oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-8-benzyl-3-[(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylbutanoyl]oxazolidin-2-one

There total 5 articles about (S)-8-benzyl-3-[(2S,3R)-3-(tert-butyldimethylsilyloxy)-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: 97.0%

t-butyldimethylsiyl triflate (69739-34-0) + (4S,2'S,3'R)-3-(3'-hydroxy-2'-methylbutanoyl)-4-benzyl-2-oxazolidinone (101711-79-9) → (S)-8-benzyl-3-[(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylbutanoyl]oxazolidin-2-one (101711-80-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1039/c2ob26185e

Reference yield: 38.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (4S,2'R,3'S)-3-(3'-hydroxy-2'-methylbutanoyl)-4-benzyl-2-oxazolidinone → (S)-8-benzyl-3-[(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylbutanoyl]oxazolidin-2-one (101711-80-2)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; Inert atmosphere; Schlenk technique;

DOI:10.1039/c6cc10172k

Reference yield:

(S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8) → (S)-8-benzyl-3-[(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylbutanoyl]oxazolidin-2-one (101711-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-Bu₂BOTf, Et₃N; 3.) H₂O₂, pH 7 buffer / 1.) 0 deg C; 2.) -78 deg C; 3.) MeOH, 0 deg C

2: imidazole / dimethylformamide

With 1H-imidazole; pH 7 buffer; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/ja00269a073

upstream raw materials:

tert-butyldimethylsilyl chloride

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

(S)-4-benzyl-3-propionyl-2-oxazolidinone

(S)-3-acryloyl-4-benzyloxazolidin-2-one