5-Thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid, 3-[(1S)-1,4-dihydroxybutyl]-8-oxo-7-[(phenylacetyl)amino]-, diphenylmethyl ester, (2R,6R,7R)-

Base Information

• Chemical Name: 5-Thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid, 3-[(1S)-1,4-dihydroxybutyl]-8-oxo-7-[(phenylacetyl)amino]-, diphenylmethyl ester, (2R,6R,7R)-
• CAS No.: 395660-95-4
• Molecular Formula: C₃₂H₃₂N₂O₆S
• Molecular Weight: 572.682
• Mol file: 395660-95-4.mol

Synonyms:

Chemical Property of 5-Thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid, 3-[(1S)-1,4-dihydroxybutyl]-8-oxo-7-[(phenylacetyl)amino]-, diphenylmethyl ester, (2R,6R,7R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid, 3-[(1S)-1,4-dihydroxybutyl]-8-oxo-7-[(phenylacetyl)amino]-, diphenylmethyl ester, (2R,6R,7R)-

There total 1 articles about 5-Thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid, 3-[(1S)-1,4-dihydroxybutyl]-8-oxo-7-[(phenylacetyl)amino]-, diphenylmethyl ester, (2R,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)-3-formyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid benzhydryl ester (39914-26-6) + 1-chloro-3-hydroxypropane (627-30-5) → diphenylmethyl (4R, 6R, 7R)-3-((1R)-1,4-dihydroxybut-1-yl)-7-phenylacetamidoceph-2-em-4-carboxylate (395660-96-5) + diphenylmethyl (4R, 6R, 7R)-3-((1S)-1,4-dihydroxybut-1-yl)-7-phenylacetamidoceph-2-em-4-carboxylate (395660-95-4)

Guidance literature:

1-chloro-3-hydroxypropane; With methylmagnesium bromide; In tetrahydrofuran; diethyl ether; at -20 ℃; for 0.25h;

With magnesium; ethylene dibromide; In tetrahydrofuran; diethyl ether; at 60 ℃; for 0.666667h;

(6R)-3-formyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid benzhydryl ester; With lithium chloride; In tetrahydrofuran; diethyl ether; at -76 ℃; for 1.08333h;

Reference yield:

diphenylmethyl (4R, 6R, 7R)-3-((1S)-1,4-dihydroxybut-1-yl)-7-phenylacetamidoceph-2-em-4-carboxylate (395660-95-4) → diphenylmethyl (4R, 6R, 7R)-7-phenylacetamido-3-[(S)-tetrahydrofuran-2-yl]ceph-2-em-4-carboxylate (395660-97-6)

Guidance literature:

With triethylamine; Methanesulfonic anhydride; In dichloromethane; at -76 ℃; for 0.25h;

Reference yield:

diphenylmethyl (4R, 6R, 7R)-3-((1S)-1,4-dihydroxybut-1-yl)-7-phenylacetamidoceph-2-em-4-carboxylate (395660-95-4) → diphenylmethyl (4R, 6R, 7R)-7-phenylacetamido-3-[(S)-tetrahydrofuran-2-yl]ceph-2-em-4-carboxylate (395660-97-6) + diphenylmethyl (4R, 6R, 7R)-7-phenylacetamido-3-[(R)-tetrahydrofuran-2-yl]ceph-2-em-4-carboxylate (395660-98-7)

Guidance literature:

With toluene-4-sulfonic acid; In ethyl acetate; at 20 ℃; for 2.5h;

upstream raw materials:

(6R)-3-formyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid benzhydryl ester

1-chloro-3-hydroxypropane

Downstream raw materials:

diphenylmethyl (4R, 6R, 7R)-7-phenylacetamido-3-[(S)-tetrahydrofuran-2-yl]ceph-2-em-4-carboxylate

diphenylmethyl (4R, 6R, 7R)-7-phenylacetamido-3-[(R)-tetrahydrofuran-2-yl]ceph-2-em-4-carboxylate