80629-46-5

Basic information

• Product Name: Methyl (2S-(2alpha,5alpha,6alpha,6(S*)))-6-bromo-6-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
• CAS NO: 80629-46-5
• Molecular Weight: 338.222
• Mol File: 80629-46-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Methyl (2S-(2alpha,5alpha,6alpha,6(S*)))-6-bromo-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,6(S*)))-6-bromo-6-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate(80629-46-5)
• EPA Substance Registry System: Methyl (2S-(2alpha,5alpha,6alpha,6(S*)))-6-bromo-6-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate(80629-46-5)

Safety Data

• Hazardous Substances Data: 80629-46-5(Hazardous Substances Data)

Upstream product

• 75-16-1 methylmagnesium bromide 
• 75-07-0 acetaldehyde 
• 24138-27-0 methyl dibromopenicillanate 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 551-16-6 6-Aminopenicillanic Acid 
• 24138-27-0 methyl-6,6-dibromopenicillanate 
• 104862-33-1 (2S,5R,6R)-6-Bromo-6-iodo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 

Downstream Products

• 76431-34-0 (2S,5R,6S)-3,3-Dimethyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 
• 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 

Relevant articles and documents

STEREOSELECTIVITY IN 6-HALOPENICILLANATE GRIGNARD REACTIONS

Structural modifications of 6-halopenicillanate Grignards result in increased "aldol" stereoselectivity.The intermediacy of tetrahedral penicillin carbanions in THF and β-lactam enolates in CH2Cl2/toluene is proposed.

AN EFFICIENT SYNTHESIS OF 2-SUBSTITUTED-THIO-6-HYDROXYETHYL-PENEM-3-CARBOXYLIC ACIDS VIA 2-THIOXOPENAMS

Allyl and p-nitrobenzyl (5R,6S)-6-((R)-1-(t-butyldimethylsilyloxy)ethyl)-2-thioxopenam-3-carboxylates (19) were synthesized by base mediated cyclization of the corresponding 1-carboxylmethyl-4-phenoxy(thiocarbonyl)thio-2-azetidinones (16).The thioxopenams underwent alkylation and Michael reactions to produce 2-alkylthio- and 2-alkenylthio-penem derivatives 20 and 21.