5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-hydroxy-8-oxo-7-[(phenoxyacetyl)amino]-, (4-nitrophenyl)methyl ester, (6R,7R)-

Base Information

• Chemical Name: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-hydroxy-8-oxo-7-[(phenoxyacetyl)amino]-, (4-nitrophenyl)methyl ester, (6R,7R)-
• CAS No.: 57562-43-3
• Molecular Formula: C₂₂H₁₉N₃O₈S
• Molecular Weight: 485.474
• Mol file: 57562-43-3.mol

Synonyms:

Chemical Property of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-hydroxy-8-oxo-7-[(phenoxyacetyl)amino]-, (4-nitrophenyl)methyl ester, (6R,7R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-hydroxy-8-oxo-7-[(phenoxyacetyl)amino]-, (4-nitrophenyl)methyl ester, (6R,7R)-

There total 1 articles about 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-hydroxy-8-oxo-7-[(phenoxyacetyl)amino]-, (4-nitrophenyl)methyl ester, (6R,7R)- 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:

(6R,7R)-3-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-nitro-benzyl ester (63427-57-6) → (6R,7R)-3-Hydroxy-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester (57562-43-3)

Guidance literature:

With Lawessons reagent; ozone; Yield given. Multistep reaction; 1.) CH₂Cl₂, 2.) CH₂Cl₂;

DOI:10.1080/00397919608003725

Reference yield: 19.0%

allyl alcohol (107-18-6) + (6R,7R)-3-Hydroxy-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester (57562-43-3) → (7β)-3-(1-propenyloxy)-7-<(phenoxyacetyl)amino>-3-cephem-4-carboxylic acid (4-nitrophenyl)methyl ester + (6R,7R)-2-Allyl-3,8-dioxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:

With dimethyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 0.25h; Ambient temperature;

Reference yield: 13.0%

methanol (67-56-1) + (6R,7R)-3-Hydroxy-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester (57562-43-3) → (7β)-3-methoxy-7-[(phenoxyacetyl)amino]-3-cephem-4-carboxylic acid (4-nitrophenyl)methyl ester (53116-59-9) + (6R,7R)-2-Methyl-3,8-dioxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:

With dimethyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 0.333333h; Ambient temperature;

upstream raw materials:

(6R,7R)-3-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-nitro-benzyl ester

Downstream raw materials:

(7β)-3-methoxy-7-[(phenoxyacetyl)amino]-3-cephem-4-carboxylic acid (4-nitrophenyl)methyl ester

(7β)-3-(2-butynyloxy)-7-<(phenoxyacetyl)amino>-3-cephem-4-carboxylic acid (4-nitrophenyl)methyl ester

7-(phenoxyacetyl)-3-chloro-3-cephem-4-carboxylic acid p-nitrobenzyl ester

(4α,7β)-3-(2-butynyloxy)-7-<(phenoxyacetyl)amino>-2-cephem-4-carboxylic acid (4-nitrophenyl)methyl ester