6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester

Base Information

• Chemical Name: 6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester
• CAS No.: 36273-76-4
• Molecular Formula: C₂₂H₂₁N₃O₅S
• Molecular Weight: 439.492
• Mol file: 36273-76-4.mol

Synonyms:6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester

Chemical Property of 6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester

There total 5 articles about 6β-(4-nitro-benzylideneamino)-penicillanic 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: 94.0%

benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (3956-31-8,49626-54-2,64519-71-7) + 4-nitrobenzaldehdye (555-16-8) → 6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester (36273-76-4)

Guidance literature:

With magnesium sulfate; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/S0960-894X(01)00470-X

Reference yield:

6-aminopenicillanic acid benzyl ester (64519-71-7) + 4-nitrobenzaldehdye (555-16-8) → 6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester (36273-76-4)

Guidance literature:

In toluene;

Reference yield:

6ξ-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester (36273-76-4,49626-56-4) → 6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester (36273-76-4)

Guidance literature:

Multi-step reaction with 2 steps

1: DNP, TsOH*H₂O / CHCl₃; ethanol

2: benzene

With (+/-)-1,1-bis-(4-chloro-phenyl)-2-nitro-propane; toluene-4-sulfonic acid; In ethanol; chloroform; benzene;

DOI:10.1021/jo00918a003

upstream raw materials:

benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

4-nitrobenzaldehdye

6-Aminopenicillanic Acid

benzyl bromide

Downstream raw materials:

(5R)-6c-hydroxymethyl-3,3-dimethyl-6t-(4-nitro-benzylideneamino)-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester

benzyl (2S,5R,6S)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

6-[(4-nitro-benzyl)-oxy-imino]-penicillanic acid benzyl ester

(5R,5'R)-3,3,3',3'-tetramethyl-6,6'-bis-(4-nitro-benzylideneamino)-7,7'-dioxo-(5rH,6tH,5'r'H,6't'H)-[6,6']bi[4-thia-1-aza-bicyclo[3.2.0]heptyl]-2c,2'c'-dicarboxylic acid dibenzyl ester