105318-31-8

Basic information

• Product Name: (3S,4S)-3-<(1R)-1-tert-butyldimethylsilyloxythyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone
• Synonyms: (3S,4S)-3-<(1R)-1-tert-butyldimethylsilyloxythyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone
• CAS NO: 105318-31-8
• Molecular Weight: 586.781
• Mol File: 105318-31-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,4S)-3-<(1R)-1-tert-butyldimethylsilyloxythyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-3-<(1R)-1-tert-butyldimethylsilyloxythyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone(105318-31-8)
• EPA Substance Registry System: (3S,4S)-3-<(1R)-1-tert-butyldimethylsilyloxythyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone(105318-31-8)

Safety Data

• Hazardous Substances Data: 105318-31-8(Hazardous Substances Data)

Upstream product

• 105318-04-5 (3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxy>-2-azetidinone 
• 105318-06-7 (3S,4S)-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 105318-05-6 (3S,4S)-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R)-1-carboxyethyl>-2-azetidinone 
• 105318-23-8 (3S,4S)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-phenylthiocarbonylethyl]-1-carboxymethylazetidin-2-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 105318-30-7 (3S,4S)-3-<(1R)-1-hydroxyethyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 96035-98-2 (3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone 
• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 

Downstream Products

• 105344-46-5 (4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 105318-43-2 p-nitrobenzyl (4R,5R,6S)-6-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-diphenylphosphoryloxy-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate 

Relevant articles and documents

Synthetic studies of carbapenem and penem antibiotics. V. Efficient synthesis of the 1β-methylcarbapenem skeleton

An efficient synthesis of 1β-methylcarbapenem from the 1-(2- oxoazetidinyl)acetate 8 was developed by application of the Dieckmann reaction. Dieckmann-type cyclization of 8 and conversion to the enolphosphate 10 were achieved without epimerization to the 1α-methyl isomer in a one-pot procedure. Treatment with the mercaptan 22 after the phosphorylation resulted in a practical one-pot preparation of the 1β-methylcarbapenem derivative 23 from 8.