87579-79-1

Basic information

• Product Name: (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate
• Synonyms: (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate
• CAS NO: 87579-79-1
• Molecular Weight: 532.708
• Mol File: 87579-79-1.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate(87579-79-1)
• EPA Substance Registry System: (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate(87579-79-1)

Safety Data

• Hazardous Substances Data: 87579-79-1(Hazardous Substances Data)

Usage

Uses

(αR,2R)-2-(2-Benzothiazolyldithio)-α-(1-methylethenyl)-4-oxo-1-azetidineacetic Acid Diphenylmethyl Ester is used in the synthesis of 4-Sulfonylazetidin-2-ones which exhibits anti-cancer effects;Also, it is an intermediate used in the synthesis of Tazobactam Sodium Salt-15N3 (T010103), which is a labeled analogue of Tazobactam Sodium Salt (T010100), which is a β-Lactamase inhibitor, used with β-lactam antibiotics to enhance their effect.

Upstream product

• 149-30-4 2-Mercaptobenzothiazole 
• 100349-42-6 (2S,4S,5R)-3,3-dimethyl-4,7-dioxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid benzhydryl ester 
• 80353-26-0 Benzhydryl 6α-bromopenicillanate-1-oxide 
• 80353-26-0 6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide 
• 87579-78-0 diphenylmethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide 
• 205320-23-6 benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide 
• 24138-28-1 6-bromopenicillanic acid 
• 205320-26-9 6α-Bromopenicillanic acid 
• 551-16-6 6-aminopenicillanic acid 
• 74189-25-6 diphenylmethyl 6α-bromopenicillanate 
• 551-16-6 6-Aminopenicillanic Acid 
• 5350-57-2 benzophenone hydrazone 
• 100349-41-5 (2S,4S,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid benzhydryl ester 

Downstream Products

• 112151-51-6 (2S,3R)-3-Methyl-7-oxo-3-thiocyanatomethyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 85573-73-5 2β-chloromethyl-2α-methylpenicillin-3α-carboxylic acid diphenylmethyl ester 
• 89051-48-9 Benzhydryl 2β-bromomethyl-2α-methyl-6,6-dihydropenicillanate 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 85573-73-5 2β-(chloro)methyl-2α-methyl-6,6-dihydropenam-3α-carboxylic acid benzhydryl ester 
• 122661-93-2 2α-methyl-2β-[(1,2,3-triazol-1-yl)methyl]penicillin-3α-carboxylic acid diphenylmethyl ester 
• 188249-92-5 diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 182750-65-8 benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate 
• 182750-66-9 (2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester 
• 182750-64-7 benzhydryl 2β-(chloroacetoxy)methyl-1,1-dioxo-penicillanate 
• 1026477-53-1 (2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 

Relevant articles and documents

PENAM DERIVATIVES FOR TREATING BACTERIAL INFECTIONS

Novel iron chelating group conjugated penam derivatives described herein show antibacterial activity, and could be used as antibacterial agents or beta-lactamase inhibitors (BLIs) which are of value for application in combination with other antibacterial

2 β - Azidomethyl penicillanic acid dibenzoate. Preparation method of tazobactam intermediate and tazobactam

The invention provides a preparation method of 2 β -azipenicillanic acid dibenzoate, tazobactam intermediate and tazobactam. The preparation method comprises the following steps: carrying out free radical reaction in a solvent by using a reaction raw material comprising a double-sulfur open-loop compound, a stacked nitrogen source and an oxidant to obtain a product system comprising 2 β - azidomethyl penicillanic acid dibenzoate. By radical addition of the carbon-carbon double bonds of the double-sulfur ring-opening compound through the azide free radical, high-efficiency and high-selectivity synthesis of the disulphide ring-opening compound directly to 2 β - azimaapenem naphthenate is successfully realized through intramolecular radical substitution. Further, 2 β - azidomethyl penicillanic acid dibenzoate is taken as a key intermediate for synthesizing tazobactam, the yield of tazobactam is improved, and the cost is reduced.

Preparation method of tazobactam

The invention discloses a preparation method of tazobactam. The preparation method comprises the following steps: performing double oxidization on 2beta-chloromethyl penicillanic acid diphenyl methylester by adopting a solution prepared from potassium permanganate, glacial acetic acid and concentrated sulfuric acid; then loading triazole by taking crown ether as a phase transfer catalyst and taking potassium iodide as a catalyst; then performing deprotection to obtain tazobactam. Compared with the prior art, the preparation method disclosed by the invention has the advantages that although sulfur atoms are oxidized into sulfone to lower chlorine atom activity, the use of the crown ether as the phase transfer catalyst and the potassium iodide as the catalyst compensates for the inactivation well. By adopting the method, the stability of the 2beta-chloromethyl penicillanic acid diphenyl methyl ester is improved, the reaction time is shortened, the reaction yield is improved, the operation risk is lowered, and the industrial production is facilitated.