24138-27-0

Basic information

• Product Name: methyl (2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Synonyms: methyl (2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;(2S,5β)-6,6-Dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid methyl ester;Einecs 246-027-3
• CAS NO: 24138-27-0
• Molecular Formula: C₉H₁₁Br₂NO₃S
• Molecular Weight: 373.06154
• EINECS: 246-027-3
• Mol File: 24138-27-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 405.3°Cat760mmHg
• Flash Point: 198.9°C
• Appearance: /
• Density: 1.96g/cm³
• Vapor Pressure: 8.84E-07mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: methyl (2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate(24138-27-0)
• EPA Substance Registry System: methyl (2S-cis)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate(24138-27-0)

Safety Data

• Hazardous Substances Data: 24138-27-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H11Br2NO3S/c1-8(2)4(5(13)15-3)12-6(14)9(10,11)7(12)16-8/h4,7H,1-3H3/t4-,7+/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 551-16-6 6-Aminopenicillanic Acid 
• 56414-10-9 6-diazo-penicillanic acid methyl ester 
• 74-88-4 methyl iodide 
• 653-89-4 penicillin G methyl ester 
• 73107-23-0 6β-(nitroso-phenylacetyl-amino)-penicillanic acid methyl ester 
• 26631-90-3 brobactam 

Downstream Products

• 80629-46-5 methyl 6-α-bromo-6-β-<(1R)-hydroxyethyl>penicillanate 
• 80629-51-2 methyl (3S,5R,6R)-6-bromo-6-<(S)-1-hydroxyethyl>penicillanate 
• 76431-32-8 (2S,5R,6S)-6-Bromo-6-((S)-1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 
• 80575-10-6 methyl (3S,5R,6R)-6-bromo-6-<(R)-1-hydroxyethyl>penicillanate 
• 112335-54-3 (2S,5R,6S)-6-Acetyl-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 
• 76581-81-2 methyl (3S,5R,6S)-6-<(R)-1-hydroxyethyl>penicillanate 
• 76431-36-2 methyl (2α,3β(R*))-2-chloro-α,4-dioxo-3-(1-{[(2,2,2-trichloroethoxy)carbonyl]oxy}ethyl)azetidine-1-acetate 
• 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 
• 76431-34-0 (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 

Relevant articles and documents

Novel stereoselective synthesis of 4-acetoxyazetidinone from methyl 6,6-dibromopenicillanate: Key intermediate for the preparation of carbapenem antibiotics

A novel and practical process for the completely stereoselective synthesis of carbapenem key intermediate (3R,4R)-4-acetoxy-3-[(R)-1-((t- butyldimethylsilyl)oxy)ethyl]-2-azetidinone has been developed by starting from methyl 6,6-dibromopenicillanate. Aldol condensation of the magnesium enolate derived from the-sulfoxide with acetaldehyde allows for the stereospecific introduction of a 1-R-hydroxyethyl substituent as C-6. The hydroxyethylated product was reduced with Zn-NH4OAc in tetrahydrofuran (THF) efficiently to give methyl 6-(1-hydroxyethyl)-penicillanate-1-oxide. Protection of the hydroxy group followed by treatment with 2-mercaptobenzothiazole afforded the dithioazetidinone, which was easily reduced and methylated to give 4-methylthioazetidinone. Then this compound was oxidized with permanganate to selectively remove the side chain at the N-position to afford the 4-methylthioazetidinone derivative. A facile conversion of the methylthio group to acetoxy for a practical synthesis of 4-acetoxyazetidinone was also reported. This method provided an efficient and cost-effective process with good overall yield and excellent stereoselectivity.

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.

SYNTHESIS OF OPTICALLY ACTIVE PENEMS

A general synthesis for optically active penems is described.Penems undergo a novel thermal isomerisation reaction.