PS-5 p-nitrobenzyl ester S-oxide

Base Information

• Chemical Name: PS-5 p-nitrobenzyl ester S-oxide
• CAS No.: 76217-37-3
• Molecular Formula: C₂₀H₂₃N₃O₇S
• Molecular Weight: 449.485
• Mol file: 76217-37-3.mol

Synonyms:PS-5 p-nitrobenzyl ester S-oxide

Chemical Property of PS-5 p-nitrobenzyl ester S-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of PS-5 p-nitrobenzyl ester S-oxide

There total 2 articles about PS-5 p-nitrobenzyl ester S-oxide 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: 90.0%

p-Nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (71730-34-2) → PS-5 p-nitrobenzyl ester S-oxide (76217-37-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -35 ℃; for 0.75h;

DOI:10.1016/S0040-4039(00)86977-4

Reference yield:

4-nitrobenzyl chloride (619-73-8) → PS-5 p-nitrobenzyl ester S-oxide (76217-37-3)

Guidance literature:

Multi-step reaction with 2 steps

2: peracid oxidation

DOI:10.1016/S0040-4039(00)85790-1

Reference yield: 83.7%

2-(pyridin-4-yl)ethanethiol (2127-05-1) + PS-5 p-nitrobenzyl ester S-oxide (76217-37-3) → (5R,6R)-6-Ethyl-7-oxo-3-(2-pyridin-4-yl-ethylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (81488-28-0)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at -35 ℃; for 0.166667h;

DOI:10.1016/S0040-4039(00)86977-4

upstream raw materials:

p-Nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

4-nitrobenzyl chloride

Downstream raw materials:

(5R,6R)-3-(2-Dimethylamino-ethylsulfanyl)-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(5R,6R)-6-Ethyl-7-oxo-3-(quinolin-8-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(5R,6R)-3-Cyclohexylsulfanyl-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(5R,6R)-6-Ethyl-7-oxo-3-(2-pyridin-4-yl-ethylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Refernces

• 1、 Yoshioka,Kojima,Isshiki,et al.. "Structures of OA-6129A, B1, B2 and C, new carbapenem antibiotics". . p. 5177 - 5180. Retrieved 2007/10/02.