p-nitrobenzyl 4-[(2R,3S)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

Base Information

• Chemical Name: p-nitrobenzyl 4-[(2R,3S)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate
• CAS No.: 80559-34-8
• Molecular Formula: C₂₄H₂₃N₃O₁₁
• Molecular Weight: 529.46
• Mol file: 80559-34-8.mol

Synonyms:p-nitrobenzyl 4-[(2R,3S)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

Chemical Property of p-nitrobenzyl 4-[(2R,3S)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl 4-[(2R,3S)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

There total 27 articles about p-nitrobenzyl 4-[(2R,3S)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate 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:

methyl 3-methyl-2-[(3S,4R)-4-{2-(p-nitrobenzyloxycarbonylmethyl)allyl}-3-[(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]but-2-enoate (80528-33-2) → p-nitrobenzyl 4-[(2R,3S)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate (80559-34-8)

Guidance literature:

With dimethylsulfide; ozone; Yield given. Multistep reaction; 1.) Ethylacetate, -78 deg C, 2.) CH₂Cl₂, MeOH, 0 to 25 deg C, 4 h and 50 deg C, 6 h;

DOI:10.1016/S0040-4039(00)87743-6

Reference yield:

methyl 3-methyl-2-[(3S,4R)-4-{2-(p-nitrobenzyloxycarbonylmethyl)allyl}-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-but-2-enoate (80559-33-7) → p-nitrobenzyl 4-[(2R,3S)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate (80559-34-8)

Guidance literature:

With dimethylsulfide; In methanol; dichloromethane; ethyl acetate;

Reference yield:

(+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one (77447-98-4) → (+/-)-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-4β-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)azetidin-2-one (76347-45-0,77448-01-2,80559-34-8,80559-36-0,92693-50-0,133443-88-6)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. acetic acid / Heating

2: Jones reagent

3: 1.) N,N'-carbonyldiimidazole

With jones reagent; acetic acid; 1,1'-carbonyldiimidazole;

upstream raw materials:

magnesium 4-nitrobenzyl malonate

(6RS,7SR)-7-acetyl-8-oxo-3-oxa-1-aza-bicyclo[4.2.0]octane-2-spirocyclohexane

(6RS,9RS)-7-chloro-7-(1-hydroxyethyl)-8-oxo-3-oxa-1-azabicyclo<4.2.0>octane-2-spirocyclohexane

7-acetyl-7-chloro-8-oxo-3-oxa-1-azabicyclo<4.2.0>octane-2-spirocyclohexane

Downstream raw materials:

(+/-)-p-nitrobenzyl 6α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

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

(+/-)-p-nitrobenzyl 6α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

(+/-)-p-nitrobenzyl 3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate