(2S,4S,9R)-4-benzyl-2-propionyl-oxazolidine-3-carboxylic acid-3-tert-butyl ester

Base Information

• Chemical Name: (2S,4S,9R)-4-benzyl-2-propionyl-oxazolidine-3-carboxylic acid-3-tert-butyl ester
• CAS No.: 362632-11-9
• Molecular Formula: C₁₈H₂₇NO₄
• Molecular Weight: 321.417
• Mol file: 362632-11-9.mol

Synonyms:(2S,4S,9R)-4-benzyl-2-propionyl-oxazolidine-3-carboxylic acid-3-tert-butyl ester

Chemical Property of (2S,4S,9R)-4-benzyl-2-propionyl-oxazolidine-3-carboxylic acid-3-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,9R)-4-benzyl-2-propionyl-oxazolidine-3-carboxylic acid-3-tert-butyl ester

There total 6 articles about (2S,4S,9R)-4-benzyl-2-propionyl-oxazolidine-3-carboxylic acid-3-tert-butyl 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: 72.0%

(4S,2S)-4-benzyl-2-propionyl-oxazolidine-3-carboxylic acid-3-tert-butyl ester (362632-09-5) → (2S,4S,9R)-4-benzyl-2-propionyl-oxazolidine-3-carboxylic acid-3-tert-butyl ester (362632-11-9) + (2S,4S,9S)-4-benzyl-2-propionyl-oxazolidine-3-carboxylic acid-3-tert-butyl ester (362632-10-8)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)00458-6

Reference yield:

L-Phenylalaninol (3182-95-4) → (2S,4S,9R)-4-benzyl-2-propionyl-oxazolidine-3-carboxylic acid-3-tert-butyl ester (362632-11-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 5.45 g / LiOH

2: 79 percent / isobutyl chloroformiate; HCl

3: 72 percent / diethyl ether / 0.5 h / 20 °C

4: 54 percent / CeCl₃; NaBH₄ / ethanol / 0.5 h / -78 °C

With hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; isobutyl chloroformate; In diethyl ether; ethanol;

DOI:10.1016/S0040-4020(01)00458-6

Reference yield:

(2S,4S)-4-Benzyl-oxazolidine-2-carboxylic acid ethyl ester → (2S,4S,9R)-4-benzyl-2-propionyl-oxazolidine-3-carboxylic acid-3-tert-butyl ester (362632-11-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 5.45 g / LiOH

2: 79 percent / isobutyl chloroformiate; HCl

3: 72 percent / diethyl ether / 0.5 h / 20 °C

4: 54 percent / CeCl₃; NaBH₄ / ethanol / 0.5 h / -78 °C

With hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; isobutyl chloroformate; In diethyl ether; ethanol;

DOI:10.1016/S0040-4020(01)00458-6

upstream raw materials:

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

L-Phenylalaninol

(4S,2S)-4-benzyl-oxazolidinone-2,3-dicarboxylic acid-3-tert-butyl ester

(4S,2S)-4-benzyl-2-(methoxy-methyl-carbamoyl)-oxazolidine-3-carboxylic acid-3-tert-butyl ester

Downstream raw materials:

(3S,6S,7RS)-3-benzyl-6-ethyl-tetrahydro-1,5-dioxa-3a-aza-pentalen-4-one

(4R,5R,6S)-4-allyl-3-(1-benzyl-2-hydroxy-ethyl)-5-ethyl-oxazolidin-2-one

(4R,5R,6S)-2-(4-allyl-5-ethyl-2-oxo-oxazolidin-3-yl)-3-phenyl-propionaldehyde