90694-08-9

Upstream product

• 80675-54-3 ((1-(phenylthio)vinyl)oxy)trimethylsilane 
• 97033-08-4 Acetic acid (2R,3R)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester 
• 90628-92-5 phenyl thiolester 
• 90629-38-2 (3S,4R)-3-[(R)-1-Hydroxyethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone 
• 4457-32-3 4-nitrobenzyl chloroformate 
• 86978-81-6 (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone 
• 108-98-5 thiophenol 
• 76335-76-7 (+/-)-4β-carboxymethyl-3α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one 
• 64066-71-3 (3S,4R)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-(2-oxoethyl)-2-oxoazetidine 
• 72789-82-3 (3S,4R)-4-(2,2-dimethoxyethyl)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-oxoazetidine 
• 98729-75-0 Carbonic acid (R)-1-[(3S,4S)-1-(4-methoxy-benzyl)-2-oxo-4-phenylsulfanylethynyl-azetidin-3-yl]-ethyl ester 4-nitro-benzyl ester 
• 98076-60-9 t-butyl (2S,3S)-1-(4-methoxybenzyl)-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-4-oxo-2-azetidinecarboxylate 
• 98076-61-0 (2S,3S)-1-(4-methoxybenzyl)-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-4-oxo-2-azetidinecarboxylic acid 
• 98076-58-5 (2S,3S)-3-<(R)-1-hydroxyethyl>-1-(4-methoxybenzyl)-4-oxo-2-azetidinecarboxylic acid 

Downstream Products

• 90629-11-1 {(3S,4R)-3-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-2-oxo-4-phenylsulfanylcarbonylmethyl-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester 
• 78072-35-2 (+/-)-p-nitrobenzyl 6α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 
• 78072-34-1 (+/-)-3α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-1--4β-<(phenylthio)carbonylmethyl>azetidin-2-one 
• 90629-15-5 (3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone 
• 78072-35-2 (5R,6S)-6-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 102735-71-7 (3S,4R)-4-<<2-(p-nitrobenzyloxycarbonylamino)etylthio>carbonylmethyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone 
• 78072-37-4 Hydroxy-{(3S,4R)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-2-oxo-4-phenylsulfanylcarbonylmethyl-azetidin-1-yl}-acetic acid 4-nitro-benzyl ester 

Relevant academic research and scientific papers

Azetidinone derivatives, a process for their preparation and their use as intermediates in the preparation of carbapenem antibiotics

Compounds of formula (I): STR1 (wherein R1 represents hydrogen or a hydroxy-protecting group, R2 and R3 represent hydrogen, alkyl or aryl; R4 represents optionally substituted alkyl, alicyclic heterocyclic, aryl

CYCLIZATION REACTION OF N-PROPARGYL EPOXYAMIDE TO ACETYLENIC 2-AZETIDINONE, A PRECURSOR TO THIENAMYCIN AND RELATED CARBAPENEMS

Base treatment of N-propargyl epoxyamide 5 afforded the acetylenic 3-(hydroxyethyl)-2-azetidinone 9a, which was subsequently transformed to phenyl thiolester 2, a versatile intermediate for the carbapenem synthesis.

REACTION OF ACETOXYAZETIDINONES WITH TRIMETHYLSILYLACETYL THIOLESTERS: PREPARATION OF AZETIDINONE-THIOLESTER PRECURSORS TO CARBAPENEMS

Reaction of acetoxyazetidinones, 1 and 2, with trimethylsilylacetyl thiolesters 10 afforded azetidinone-thiolesters, 11 and 12, which are useful intermediates in the carbapenem synthesis.

AN EFFICIENT CARBAPENEM SYNTHESIS VIA AN INTRAMOLECULAR WITTIG REACTION OF NEW TRIALKOXYPHOSPHORANE-THIOLESTERS

New trialkoxyphosphorane-thiolesters 10, obtained by reaction of oxalimides 9 with trialkyl phosphite, were efficiently cyclized by an intramolecular Wittig reaction to give carbapenems 11.

Studies on the Syntheses of Heterocyclic Compounds. Part 877. An Alternative Synthesis of Protected (+/-)-Thienamycin and a Related Compound

An alternative total synthesis of protected (+/-)-thienamycin (2) and an analogue is described. (+/-)-4β-(2,2-Dimethoxyethyl)-3α-*)-1-(-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one (5), prepared from isoxazoline derivatives (4), was conve