186459-21-2

Basic information

• Product Name: [(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((R)-1-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid allyl ester
• Synonyms: [(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((R)-1-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid allyl ester
• CAS NO: 186459-21-2
• Molecular Weight: 491.724
• Mol File: 186459-21-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((R)-1-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid allyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((R)-1-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid allyl ester(186459-21-2)
• EPA Substance Registry System: [(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((R)-1-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid allyl ester(186459-21-2)

Safety Data

• Hazardous Substances Data: 186459-21-2(Hazardous Substances Data)

Upstream product

• 158299-15-1 3-<(2R)-2-<(2R,3S)-3-<(1R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-oxoazetidin-2-yl>propionyl>spiro-<2,3-dihydro-4H-1,3-benzoxazine-2,1'-cyclohexan>-4-one 
• 107514-91-0 (3S,4R)-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<(tert-butyldimethylsilyl)oxy>carbonyl>ethyl>azetidin-2-one 
• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 108-98-5 thiophenol 
• 153976-18-2 (3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-carboxyethyl]-2-azetidinone 

Relevant articles and documents

Efficient synthesis of 1β-methylcarbapenems based on the counter-attack strategy

A seven-step efficient synthesis of 1β-methylcarbapenems 1 from the acetoxyazetidinone 6 is described. The Reformatsky reaction of 3-(2-bromopropionyl)-1,3-benzoxazinone 7 with compound 6 gave an adduct 8 in 96% yield with high β-selectivity (β:α = 92:8). Compound 8 was transformed in three steps into the side-chain thiol esters 12a-e in good yields. The chlorotrimethylsilane-mediated Dieckmann-type cyclisation of thioesters 12b-e followed by counter-attack of the liberated thiolate anion 18 yielded the C-2 alkylthio- or arylthio-substituted 1β-methylcarbapenems 19b-e in a one-pot procedure. The synthesis of 1β-methylcarbapenems 1 was demonstrated by a simple cleavage of the silyl ether and allyl ester of compound 19b to afford target compound 1b in high yield.