161692-28-0

Basic information

• Product Name: (4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• Synonyms: (4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• CAS NO: 161692-28-0
• Molecular Weight: 666.697
• Mol File: 161692-28-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate(161692-28-0)
• EPA Substance Registry System: (4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate(161692-28-0)

Safety Data

• Hazardous Substances Data: 161692-28-0(Hazardous Substances Data)

Upstream product

• 105318-30-7 (3S,4S)-3-<(1R)-1-hydroxyethyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 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 
• 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 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 105318-32-9 (3S,4S)-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-3-<(1R)-1-trimethylsilyloxyethyl>-2-azetidinone 

Downstream Products

• 96036-02-1 p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate 
• 189150-85-4 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-[4-(1,2,3,4-tetrahydro-isoquinolin-7-yl)-thiazol-2-ylsulfanyl]-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 189150-49-0 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-(4-{4-[(4-nitro-benzyloxycarbonylamino)-methyl]-phenyl}-thiazol-2-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 161681-69-2 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-{4-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-thiazol-2-ylsulfanyl}-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 161681-70-5 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-{4-[3-(4-methyl-piperazine-1-carbonyl)-phenyl]-thiazol-2-ylsulfanyl}-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 161681-68-1 (4R,5S,6S)-3-{4-[4-(2-Dimethylamino-ethylcarbamoyl)-phenyl]-thiazol-2-ylsulfanyl}-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 161681-74-9 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-[4-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-thiazol-2-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 189150-71-8 (4R,5S,6S)-3-[4-(4-Carbamoyl-phenyl)-thiazol-2-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 189150-65-0 (4R,5S,6S)-3-[4-(3-Carbamoyl-phenyl)-thiazol-2-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 161681-66-9 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-(4-isoquinolin-7-yl-thiazol-2-ylsulfanyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 189150-38-7 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-[4-(2-nitro-phenyl)-thiazol-2-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 

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.