p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• CAS No.: 80951-83-3
• Molecular Formula: C₂₀H₂₃N₃O₇S
• Molecular Weight: 449.485
• Mol file: 80951-83-3.mol

Synonyms:p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Chemical Property of p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

There total 12 articles about p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 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: 37.0%

p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-formyloxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (82922-52-9) → p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (80951-83-3) + p-nitrobenzyl (5R)-3-(2-acetamidoethylthio)-6-(E)-ethylidene-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (73521-63-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 0 ℃; for 0.0833333h;

Reference yield:

(3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one (74288-39-4) → p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (80951-83-3)

Guidance literature:

Multi-step reaction with 3 steps

1: dirhodium tetraacetate / toluene

2: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile

3: N-ethyl-N,N-diisopropylamine

With dmap; dirhodium tetraacetate; N-ethyl-N,N-diisopropylamine; In toluene; acetonitrile;

DOI:10.1021/ol901269d

Reference yield:

(3S,4R)-3-<(R)-1'-(dimethyl-t-butylsilyloxy)ethyl>-4-oxoazetidin-2-carboxylic acid (115936-64-6) → p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (80951-83-3)

Guidance literature:

Multi-step reaction with 6 steps

1: lead(IV) tetraacetate / N,N-dimethyl-formamide

2: zinc(II) chloride / dichloromethane

3: hydrogenchloride; methanol

4: dirhodium tetraacetate / toluene

5: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile

6: N-ethyl-N,N-diisopropylamine

With hydrogenchloride; methanol; dmap; dirhodium tetraacetate; lead(IV) tetraacetate; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ol901269d

upstream raw materials:

p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-formyloxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

(3S,4R)-benzyl N-(p-toluenesulfonyl)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-azetidin-2-one-4-carboxylate

(3S,4R)-benzyl 3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-azetidin-2-one-4-carboxylate

2-(acetylamino)ethanethiol

Downstream raw materials:

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

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