59054-27-2

Basic information

• Product Name: (3S,5R,6R)-monomethyl benzylpenicilloate
• Synonyms: (3S,5R,6R)-monomethyl benzylpenicilloate
• CAS NO: 59054-27-2
• Molecular Weight: 366.438
• Mol File: 59054-27-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 607.5±55.0 °C(Predicted)
• Density: 1.262±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (3S,5R,6R)-monomethyl benzylpenicilloate(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5R,6R)-monomethyl benzylpenicilloate(59054-27-2)
• EPA Substance Registry System: (3S,5R,6R)-monomethyl benzylpenicilloate(59054-27-2)

Safety Data

• Hazardous Substances Data: 59054-27-2(Hazardous Substances Data)

Usage

General Description

"(3S,5R,6R)-monomethyl benzylpenicilloate" is a semi-synthetic derivative of the antibiotic benzylpenicillin. It is classified as a β-lactam antibiotic and is commonly used to treat bacterial infections. The chemical structure of this compound contains a β-lactam ring, which is responsible for its antibacterial activity. The addition of a monomethyl group to benzylpenicillin increases its stability and extends its spectrum of activity against a broader range of bacteria. This modification also reduces the likelihood of the antibiotic being degraded by bacterial enzymes, improving its efficacy. Overall, "(3S,5R,6R)-monomethyl benzylpenicilloate" is an important and effective antibiotic in the treatment of various bacterial infections.

Upstream product

• 52-67-5 3,3-dimethyl-D-cysteine 
• 854851-32-4 3-oxo-2-(2-phenyl-acetylamino)-propionic acid methyl ester 
• 67-56-1 methanol 
• 61-33-6 penicillin G 

Downstream Products

• 87492-68-0 (5R,6S,3S)-benzyl-D-penicilloic acid 

Relevant articles and documents

Thiazolidine Ring Opening in Penicillin Derivatives. Part 2. Enamine Formation

The alkaline hydrolysis of (3S,5R,6R)-methyl benzylpenicilloate, and the corresponding carboxamide and N-ethylamide, is accompanied by an absorbance increase at 285 nm.This is attributed to a competing elimination reaction across C6-C5 to open the thiazolidine ring and reversibly generate an enamine intermediate.Kinetic analysis and hydrolysis in D2O do not indicate a significant buildup of this intermediate during hydrolysis of the methyl ester.However, over the pH range 4-11 the rate of thiazolidine ring opening is competitive with hydrolysis of the ester function.The deuterium solvent kinetic isotope effect on the ring closure reaction is 7.5.

pH dependence of and kinetic solvent isotope effects on the methanolysis and hydrolysis of beta-lactams catalyzed by class C beta-lactamase

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Alcohol-catalysed Hydrolysis of Benzylpenicillin

The hydrolysis of benzylpenicillin is catalysed by alkoxide ions and other oxygen bases.Catalysis occurs by a nucleophilic pathway and the intermediate ester can be detected in some cases.The Broensted βnuc for alkoxide ions is 0.97, and is compatible with rate-limiting ring opening of the β-lactam.A solvent isotope effect of 3.2 for the trifluoroethanol-catalysed reaction suggests protonation by water occurs to the departing β-lactam nitrogen.Penicillin in not a particularly effective acylating agent of alcohols.