10209-10-6

Basic information

• Product Name: diphenylmethyl (6R-trans)-3-methyl-8-oxo-7-(phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Synonyms: diphenylmethyl (6R-trans)-3-methyl-8-oxo-7-(phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;(6R)-3-Methyl-8-oxo-7α-(phenyloxyacetylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester;(6β)-3-Methyl-7α-[(phenoxyacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid diphenylmethyl ester
• CAS NO: 10209-10-6
• Molecular Formula: C₂₉H₂₆N₂O₅S
• Molecular Weight: 514.59214
• EINECS: 233-510-9
• Mol File: 10209-10-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 773.9°Cat760mmHg
• Flash Point: 421.9°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 6.97E-24mmHg at 25°C
• Refractive Index: 1.678
• CAS DataBase Reference: diphenylmethyl (6R-trans)-3-methyl-8-oxo-7-(phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: diphenylmethyl (6R-trans)-3-methyl-8-oxo-7-(phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate(10209-10-6)
• EPA Substance Registry System: diphenylmethyl (6R-trans)-3-methyl-8-oxo-7-(phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate(10209-10-6)

Safety Data

• Hazardous Substances Data: 10209-10-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C29H26N2O5S/c1-19-18-37-28-24(30-23(32)17-35-22-15-9-4-10-16-22)27(33)31(28)25(19)29(34)36-26(20-11-5-2-6-12-20)21-13-7-3-8-14-21/h2-16,24,26,28H,17-18H2,1H3,(H,30,32)/t24-,28-/m1/s1

Upstream product

• 143159-88-0 Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate 
• 37591-67-6 (1S,3S,5R,6R) 2,2-Dimethyl-6-phenoxyacetamidopenam-3-carboxylic acid-1-oxide diphenylmethyl ester 
• 186099-10-5 (1S,3S,5R,6R) 2,2-dimethyl-6-phenoxyacetamidopenam-3-carboxylic acid-1-oxide diphenylmethyl ester monohydrate 
• 4083-64-1 Tosyl isocyanate 
• 506-96-7 Acetyl bromide 
• 5587-61-1 triisocyanato(methyl)silane 
• 5587-62-2 dimethylsilyl diisocyanate 
• 3998-25-2 acetyl isocyanate 
• 57561-92-9 benzhydryl 3-hydroxy-7β-(2-phenoxyacetamido)-Δ³-cephem-4-carboxylate 
• 143159-86-8 Diphenylmethyl 2-<(3R,4R)-4-<(p-toluenesulfonyl)thio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate 
• 130516-07-3 diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<<(trifluoromethyl)sulfonyl>oxy>ceph-3-em-4-carboxylate 
• 66680-84-0 (Z)-1-propenyltributyltin 
• 15681-48-8 lithium dimethylcuprate 
• 130516-09-5 (6R,7R)-3-(4-Nitro-benzenesulfonyloxy)-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 

Downstream Products

• 99346-43-7 (2S,6R,7R)-diphenylmethyl 2-ethoxy-3-methyl-7-phenoxyacetamidoceph-3-em-4-carboxylate 
• 66493-10-5 (2S,6R,7R)-diphenylmethyl 2-methoxy-3-methyl-7-phenoxyacetamidoceph-3-em-4-carboxylate 
• 121406-71-1 (Z)-2-[2-Benzhydryloxycarbonyl-3-methyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-3-en-2-yl]-but-2-enedioic acid dimethyl ester 
• 121406-72-2 2-[2-Benzhydryloxycarbonyl-3-methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-en-2-yl]-succinic acid dimethyl ester 
• 121406-63-1 (6R,7R)-3-Methyl-5,8-dioxo-2-(3-oxo-butyl)-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester 
• 121406-64-2 (6R,7R)-3-Methyl-5,8-dioxo-2-(3-oxo-butyl)-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 
• 121406-62-0 (6R,7R)-3-Methyl-8-oxo-2-(3-oxo-butyl)-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 
• 121406-65-3 N-[(6R,7R)-3-Methyl-5,8-dioxo-2-(3-oxo-butyl)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-en-7-yl]-2-phenoxy-acetamide 
• 134930-74-8 diphenylmethyl (1S,6R,7R)-3-methyl-4-(3'-oxobutyl)-7β-phenoxyacetamidoceph-2-em-4-carboxylate 1-oxide 
• 134527-24-5 diphenylmethyl (6R,7R)-4-(4'-methoxycarbonylethyl)-3-methyl-7β-phenoxyacetamidoceph-2-em-4-carboxylate 
• 134931-68-3 (1S,6R,7R)-3-methyl-4-(3'-oxobutyl)-7β-phenoxyacetamidoceph-2-em-4-carboxylic acid 1-oxide 
• 134853-40-0 (6R,7R)-4-<1',2'-bis(methoxycarbonyl)vinyl>-3-methyl-7β-phenoxyacetamidoceph-3-em 
• 135026-79-8 (6R,7R)-3-methyl-4-(3'-oxobutyl)-7β-phenoxyacetamidoceph-2-em-4-carboxylic acid 
• 134830-17-4 (1S,6R,7R)-4-(2'-methoxycarbonylethyl)-3-methyl-7β-phenoxyacetamidoceph-3-em 1-oxide 

Relevant articles and documents

A stereocontrolled synthesis of cefprozil and related cephems via allenylazetidinones

A new method for the preparation of cephalosporins bearing carbon substituents of choice at C-3 is described. The approach involves 1,4-conjugate addition of an organocuprate to an allenylazetidinone to form a carbon-carbon bond followed by ring closure via intramolecular sulfenylation reaction.

Nucleophilic substitution of 3-fluorosulfonyloxy cephalosporins with organocuprates

3-Fluorosulfonyloxy cephems readily undergo addition-elimination reactions with organocuprates derived from the corresponding Grignard reagents. This chemistry presents an efficient, cost effective process for the preparation of 3-substituted cephems.

Reactions of organocuprates with vinyl-triflates and related cephems: A novel approach to 3-substituted cephalosporins

Vinyl-triflates and related 3-substituted cephems readily undergo addition-elimination reactions with a variety of organocuprates to form new carbon-carbon bonds. This chemistry presents a novel approach to the synthesis of 3-alkyl, 3-aryl, and 3-alkenylcephalosporins.