76517-80-1

Basic information

• Product Name: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(hydroxymethyl)-3,3-dimethyl-7-oxo-, diphenylmethyl ester, (2S,5R,6R)-
• CAS NO: 76517-80-1
• Molecular Formula: C22H23NO4S
• Molecular Weight: 397.495
• Mol File: 76517-80-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(hydroxymethyl)-3,3-dimethyl-7-oxo-, diphenylmethyl ester, (2S,5R,6R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(hydroxymethyl)-3,3-dimethyl-7-oxo-, diphenylmethyl ester, (2S,5R,6R)-(76517-80-1)
• EPA Substance Registry System: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(hydroxymethyl)-3,3-dimethyl-7-oxo-, diphenylmethyl ester, (2S,5R,6R)-(76517-80-1)

Safety Data

• Hazardous Substances Data: 76517-80-1(Hazardous Substances Data)

Upstream product

• 24158-88-1 6,6-dibromopenicillanic acid 
• 908093-98-1 diazodiphenylmethane 
• 75527-84-3 diphenylmethyl 6,6-dibromopenicillanate 
• 81324-31-4 diphenylmethyl 6β-bromo-6α-(hydroxymethyl)penicillanate 
• 229309-41-5 (2S,5R)-6-Bromo-6-hydroxymethyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 81324-43-8 (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 

Downstream Products

• 229489-99-0 (2S,3R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(2-chloro-acetoxymethyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229489-98-9 (2S,3R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(2-chloro-acetoxymethyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229490-04-4 (2S,3S,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((E)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229490-02-2 (2S,3S,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((Z)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229490-09-9 (2S,3R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(methoxyimino-methyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229490-00-0 (2S,3R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229490-01-1 (2S,3R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-formyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229489-96-7 (2S,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229490-06-6 (2S,3S,5R,6R)-3-((E)-2-Cyano-vinyl)-6-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229490-05-5 (2S,3S,5R,6R)-3-((Z)-2-Cyano-vinyl)-6-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229490-10-2 (2S,3R,5R,6R)-6-Hydroxymethyl-3-(methoxyimino-methyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 615551-73-0 (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanylmethyl)-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 615551-65-0 (2S,5R,6S)-3,3-Dimethyl-4,4,7-trioxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanylmethyl)-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 615551-64-9 (2S,5R,6S)-3,3-Dimethyl-7-oxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanylmethyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 

Relevant articles and documents

Penicillin-derived inhibitors that simultaneously target both metallo- and serine-β-lactamases

The synthesis and β-lactamase inhibitory activity of four 6-(mercaptomethyl)penicillinates and the four corresponding 6-(hydroxymethyl) penicillinates are described. These penicillins include both C6 stereoisomers as well as the sulfide and sulfone oxidation states of the penam thiazolidine sulfur. All compounds were evaluated as inhibitors of representative metallo- and serine-β-lactamases enzymes. Selected (mercaptomethyl)penicillinates are shown to inactivate both metallo- and serine-β-lactamases and to display synergism with piperacillin against β-lactamase producing strains.

6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C β-lactamases I

Five 6-(1-hydroxyalkyl)penam sulfone derivatives and two 6- (hydroxymethyl)penams were synthesized for β-lactamase inhibitor screens. The substituent effects and stereochemical requirements of 6α-and 6β-(1- hydroxyalkyl) groups for the biological activity of penam sulfone derivatives were investigated. Of these substituents, only the 6β-hydroxymethyl group of 15 improved the activity of sulbactam against both TEM-1 and AmpC β- lactamases. The sulfone moiety is required for the enhancement of the β- lactamase inhibitory activity. 6β-Hydroxymethylsulbactam (15) was able to restore the activity of piperacillin in vitro and in vivo against various β- lactamase producing microorganisms.

Process for converting 6,6-disubstituted penicillanic acid derivatives to the 6-β-congeners

6-β-Substituted penicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several β-lactam antibiotics against many β-lactamase producing bacteria, and 6-β-substituted penicillanic acid derivatives wherein the carboxy group is protected by a conventional penicillin carboxy protecting group as useful intermediates leading to said synergistic agents. A process for converting 6,6-disubstituted penicillanic acid derivatives to the corresponding 6-β-substituted penicillanic acid congeners.