76581-81-2

Basic information

• Product Name: methyl [2S-[2alpha,5alpha,6alpha(S*)]]-6-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Synonyms: methyl [2S-[2alpha,5alpha,6alpha(S*)]]-6-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;(2S,5R,6S)-6-[(R)-1-Hydroxyethyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
• CAS NO: 76581-81-2
• Molecular Formula: C₁₁H₁₇NO₄S
• Molecular Weight: 259.32198
• EINECS: 278-493-9
• Mol File: 76581-81-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl [2S-[2alpha,5alpha,6alpha(S*)]]-6-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl [2S-[2alpha,5alpha,6alpha(S*)]]-6-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate(76581-81-2)
• EPA Substance Registry System: methyl [2S-[2alpha,5alpha,6alpha(S*)]]-6-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate(76581-81-2)

Safety Data

• Hazardous Substances Data: 76581-81-2(Hazardous Substances Data)

Upstream product

• 24158-88-1 6,6-dibromopenicillanic acid 
• 24138-27-0 methyl-6,6-dibromopenicillanate 
• 551-16-6 6-Aminopenicillanic Acid 
• 24138-27-0 methyl dibromopenicillanate 
• 80629-46-5 methyl 6-α-bromo-6-β-<(1R)-hydroxyethyl>penicillanate 
• 76431-32-8 methyl 6α-bromo,6β-1'-(R)-hydroxyethyl penicillanate 

Downstream Products

• 76431-30-6 Carbonic acid (R)-1-((2R,3S)-2-ethylsulfanylthiocarbonylsulfanyl-4-oxo-azetidin-3-yl)-ethyl ester 2,2,2-trichloro-ethyl ester 
• 80575-09-3 {(2R,3S)-2-Ethylsulfanylthiocarbonylsulfanyl-4-oxo-3-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester 
• 76431-35-1 methyl (2α,3β(R*))-2-chloro-α-(isopropylidene)-4-oxo-3-(1-{[(2,2,2-trichloroethoxy)carbonyl]oxy}ethyl)azetidine-1-acetate 
• 76431-36-2 methyl (2α,3β(R*))-2-chloro-α,4-dioxo-3-(1-{[(2,2,2-trichloroethoxy)carbonyl]oxy}ethyl)azetidine-1-acetate 
• 383186-38-7 (3S,4R)-4-benzenesulfonyl-3-((1R)-1-(tert-butyldimethylsilanyloxy)-ethyl)-azetidin-2-one 
• 85281-73-8 (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone 
• 105420-43-7 (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>acetylthio>azetidin-2-one 
• 105499-98-7 (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2S)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>acetylthio>azetidin-2-one 
• 105560-92-7 (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthioazetidin-2-one 
• 87596-64-3 (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(2S)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthioazetidin-2-one 
• 81225-34-5 dl-(3R*,4S*)-3-<(1R*)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-2-one 
• 105499-99-8 (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-2-one 
• 105499-16-9 p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<((2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl)acetylthio>-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate 
• 105420-51-7 p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<((2S)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl)acetylthio>-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate 

Relevant articles and documents

From penicillin to penem and carbapenem. VII. Synthesis and antibacterial activity of penem derivatives

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FROM PENICILLIN TO PENEM AND CARBAPENEM. II. SYNTHESIS OF 3,4-DISUBSTITUTED AZETIDINONE DERIVATIVES FROM 6,6-BIS(PHENYLSELENYL)PENICILLANATE

6,6-Bis(phenylselenyl)penicillanate 2a was converted into 6-1'-(R)-hydroxyethyl substituted penicillanate 5 in high yield.Compound 5 was deselenylated to 10.Oxidation, and then the basic epimerization of cis sulfone 11 gave trans sulfone derivative 12.The trans sulfone 12 was degraded to the monocyclic β-lactams 14, 15 which are important precursors for the carbapenem synthesis.