(2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester
• CAS No.: 220569-30-2
• Molecular Formula: C₂₄H₂₇NO₅
• Molecular Weight: 409.482
• Mol file: 220569-30-2.mol

Synonyms:(2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property of (2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

There total 2 articles about (2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester 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%

(2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (220569-29-9) → (2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester (220569-30-2)

Guidance literature:

(2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester; With sodium hydrogencarbonate; ozone; In methanol; dichloromethane; at -78 ℃;

With dimethylsulfide; In methanol; dichloromethane; at -78 - 25 ℃;

DOI:10.1016/S0968-0896(98)80022-9

Reference yield:

(2S,4S)-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (191980-50-4) → (2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester (220569-30-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / -78 °C

1.2: 77 percent / tetrahydrofuran; toluene / 16 h / -78 - 25 °C

2.1: ozone; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

2.2: 95 percent / Me₂S / CH₂Cl₂; methanol / -78 - 25 °C

With potassium hexamethylsilazane; sodium hydrogencarbonate; ozone; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Metallation / 1.2: Alkylation / 2.1: ozonolysis / 2.2: Reduction;

DOI:10.1016/S0968-0896(98)80022-9

Reference yield:

(2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester (220569-30-2) → (2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester (220569-47-1)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOAc; 4 Angstroem molecular sieves; NaCNBH₃ / methanol / 25 °C

2: 610 mg / 1-hydroxybenzotriazole / toluene / 16 h / Heating

3: 90 percent / hydrogen / Pd/C / ethanol / 17 h

4: 61 percent / DMAP; pyridine / CH₂Cl₂ / 0 - 25 °C

With pyridine; dmap; 4 A molecular sieve; hydrogen; sodium acetate; sodium cyanoborohydride; benzotriazol-1-ol; palladium on activated charcoal; In methanol; ethanol; dichloromethane; toluene; 1: Alkylation / 2: Cyclization / 3: Hydrogenolysis / 4: Substitution;

DOI:10.1016/S0968-0896(98)80022-9

upstream raw materials:

(2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

(2S,4S)-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

(2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

(2S,3S)-N-[3-benzyl-1-(2-hydroxyl-1-methyl-ethyl)-2-oxo-pyrrolidin-3-yl]-methane-sulfonamide

(2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

(S)-2-((R)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenyl-butyric acid methyl ester