90628-99-2

Basic information

• Product Name: p-nitrobenzyl (5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>-amino>ethyl>thio>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• Synonyms: p-nitrobenzyl (5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>-amino>ethyl>thio>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• CAS NO: 90628-99-2
• Molecular Weight: 700.842
• Mol File: 90628-99-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: p-nitrobenzyl (5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>-amino>ethyl>thio>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: p-nitrobenzyl (5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>-amino>ethyl>thio>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate(90628-99-2)
• EPA Substance Registry System: p-nitrobenzyl (5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>-amino>ethyl>thio>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate(90628-99-2)

Safety Data

• Hazardous Substances Data: 90628-99-2(Hazardous Substances Data)

Upstream product

• 126579-18-8 p-nitrobenzyl (2S,3S,5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3--7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 126579-16-6 p-nitrobenzyl (2R,3S)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-(2-hydroxy-3-nitropropyl)-4-oxo-1-azetidineacetate 
• 108789-28-2 p-nitrobenzyl (2S,3S,5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3-(nitromethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 126579-19-9 p-nitrobenzyl (5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3-(nitromethylene)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 126579-17-7 p-nitrobenzyl (2R,3S)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-<(E)-3-nitro-2-propenyl>-4-oxo-1-azetidineacetate 
• 126579-13-3 p-nitrobenzyl (2R,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)-oxy>ethyl>-2-(2,3-dihydroxypropyl)-4-oxo-1-azetidineacetate 
• 126579-15-5 p-nitrobenzyl (3S,4R)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-oxoethyl)-1-azetidineacetate 
• 126579-11-1 p-nitrobenzyl (3S,4R)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-propenyl)-1-azetidineacetate 
• 80433-47-2 (3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-(prop-2-enyl)-2-azetidinone 
• 86978-81-6 (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone 
• 88669-70-9 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one 
• 90628-98-1 {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester 
• 90628-97-0 3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<<<2-<<(p-nitrobenzyloxy)carbonyl>amino>ethyl>thio>carbonyl>methyl>azetidin-2-one 
• 87392-18-5 <3S-<3α(S^*),4β>>-benzyl<3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate 

Downstream Products

• 64067-13-6 p-nitrobenzyl (5R,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate 

Relevant articles and documents

A Novel Ring-Closure Strategy for the Carbapenems: The Total Synthesis of (+)-Thienamycin

Intramolecular Michael cyclization of an N--4-(3-nitro-2-propenyl)-3-oxoazetidin-2-one available in optically pure form leads to the corresponding carbapenam skeleton.Further elaboration via oxidative cleavage of an exocyclic nitromethylene group gives an advanced intermediate, which was transformed into (+)-thienamycin.The stereochemistry of the Michael cyclization and the pitfalls of protective group chemistry are discussed.