54639-48-4

Basic information

• Product Name: (6R,7R)-3-Hydroxy-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenyl methyl ester
• Synonyms: GHYH;7-PHENYL ACETAMIDO-3-HYDROXY-3-CEPHEM-4-CARBOXYLIC ACID DIPHENYLMETHYL ESTER;7-PHENYLACETAMIDE-3-HYDROXY-3-CEPHEM-4-CARBOXYLIC ACID DIPHENYLMETHYL ESTER;3-hydroxy-8-oxo-7-[(phenylacetyl)amino]-,diphenylmethylester,(6R,7R)-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid;3-Oh;7-PHENYL ACETAMIDO-3-HYDROXY-3-CEPHEM-4-CARBOXYLIC ACID DIPHENYLMETHYL ESTER , 3-OH;3-hydroxy-8-oxo-7-[(phenylacetyl)amino]-, diphenylmethyl ester, (6R,7R)-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-hydroxy-8-oxo-7-[(phenylacetyl)amino]-,diphenylmethyl ester,(6R,7R)-
• CAS NO: 54639-48-4
• Molecular Formula: C₂₈H₂₄N₂O₅S
• Molecular Weight: 500.57
• EINECS: 807-963-3
• Product Categories: Organic acids
• Mol File: 54639-48-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 777.1 °C at 760 mmHg
• Flash Point: 423.8 °C
• Appearance: /
• Density: 1.42 g/cm³
• Vapor Pressure: 1.73E-21mmHg at 25°C
• Refractive Index: 1.725
• Storage Temp.: 2-8°C
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: (6R,7R)-3-Hydroxy-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenyl methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,7R)-3-Hydroxy-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenyl methyl ester(54639-48-4)
• EPA Substance Registry System: (6R,7R)-3-Hydroxy-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenyl methyl ester(54639-48-4)

Safety Data

• Hazardous Substances Data: 54639-48-4(Hazardous Substances Data)

Usage

Uses

3(6R,7R)--Hydroxy-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Diphenylmethyl Ester is a useful synthetic intermediate. It was used to prepare cephalosporin-derived inhibitors. It can also be used to synthesize Ceftaroline Fosamil which is a cephalosporin antibiotic.

InChI:InChI=1/C15H14N2O5S/c18-9-7-23-14-11(13(20)17(14)12(9)15(21)22)16-10(19)6-8-4-2-1-3-5-8/h1-5,11,14,18H,6-7H2,(H,16,19)(H,21,22)/t11?,14-/m1/s1

Upstream product

• 54240-49-2 (6R)-3-methylene-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 
• 859-07-4 cephaloram 
• 146340-04-7 1-<3-chloro-2-(diphenylmethyloxy)-1-(diphenylmethyloxycarbonyl)-1-propen-1-yl>-3-(phenylacetamido)-4-(phenylsulfonylthio)-2-azetidinone 
• 164032-75-1 diphenylmethyl 2-(3-benzyl-6-oxo-2-thia-4,7-diazabicyclo<3.2.0>hept-3-en-7-yl)-4-chloro-3-hydroxy-2-butenoate 
• 131857-35-7 1-<3-chloro-2-(diphenylmethyloxy)-1-(diphenylmethyloxycarbonyl)-1-propen-1-yl>-3-(phenylacetamido)-4-(phenylsulfonylthio)-2-azetidinone 
• 164201-44-9 1-<3-chloro-1-(diphenylmethyloxycarbonyl)-2-hydroxy-1-propen-1-yl>-3-(phenylacetamido)-4-(phenylsulfonylthio)-2-azetidinone 
• 131857-37-9 (6R,7R)-3-Benzhydryloxy-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 51762-03-9 (6R)-3-methylene-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester 

Downstream Products

• 51761-93-4 (6R)-3-methoxy-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 54639-51-9 (6R)-3-methoxyimino-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2ξ-carboxylic acid benzhydryl ester 
• 53824-89-8 N-((6R)-3,8-dioxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-7t-yl)-2-phenyl-acetamide 
• 58232-56-7 (6R)-8-oxo-7t-(2-phenyl-acetylamino)-3-(toluene-4-sulfonyloxy)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 137167-58-9 (6R,7R)-3-Fluorosulfonyloxy-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 315206-91-8 diphenylmethyl 7-phenylacetylamino-3-hydroxy-3-(1-methylprop-2-enyl)cepham-4-carboxylate 
• 315206-87-2 diphenylmethyl 7-phenylacetylamino-3-hydroxy-3-(2-methylprop-2-enyl)cepham-4-carboxylate 
• 315206-89-4 diphenylmethyl 7-phenylacetylamino-3-hydroxy-3-(2-methoxycarbonylprop-2-enyl)cepham-4-carboxylate 
• 51762-51-7 (6R)-3ξ-hydroxy-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2ξ-carboxylic acid benzhydryl ester 
• 1053243-69-8 (2R,3R,6R,7R)-3-Acetoxy-3-(2-methoxycarbonyl-allyl)-5,8-dioxo-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester 
• 1053691-09-0 (2R,3R,6R,7R)-3-Acetoxy-3-(2-methoxycarbonyl-allyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester 
• 1053259-75-8 (2R,3R,6R,7R)-3-Acetoxy-3-allyl-5,8-dioxo-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester 
• 1026502-38-4 (2R,3R,6R,7R)-3-Acetoxy-3-(1-methyl-allyl)-5,8-dioxo-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester 
• 1054624-75-7 (2R,3R,6R,7R)-3-Acetoxy-3-allyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester 

Relevant articles and documents

Synthesis of 3-hydroxycephems from penicillin G through cyclization of chlorinated 4-(phenylsulfonylthio)-2-azetidinones promoted by a BiCl3/Sn or TiCl4/Sn bimetal redox system

A novel access to 3-hydroxycephems was attained from penicillin G via the C=C bond cleavage of 1-(1-alkoxycarbonyl-2-chloromethyl-2-propenyl)-4-(phenylsulfonylthio)- 2-azetidinones by successive treatment with RuCl3/HIO4 and HIO4/CuSO4 and reductive cyclization of I-(I-alkoxycarbonyl-3-chloro-2-hydroxy-1-propenyl)-4-(phenylsulfonylth io)-2-azetidinones on treatment with a newly devised BiCl3/Sn or TiCl4/Sn bimetal redox couple in DMF containing pyridine.