93788-47-7

Upstream product

• 16029-98-4 trimethylsilyl iodide 
• 82551-63-1 4-nitrobenzyl 2-diazo-3-oxo-butanoate 
• 619-73-8 4-nitrobenzyl chloride 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 61312-84-3 4-nitrobenzyl 3-oxobutanoate 

Downstream Products

• 98269-57-9 3-(1-methylethylidene)-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone 
• 93861-39-3 (3S,4R)-3-[(1R)-(tert-butyldimethyl-silyloxy)ethyl]-4-[3-(4-nitrobenzyloxy)carbonyl-2-oxo-3-diazopropyl]azetidin-2-one 
• 112245-22-4 p-nitrobenzyl 4-{(3R,4R)-3-[(R)-1-fluoroethyl]-2-oxoazetidin-4-yl}-2-diazo-3-oxobutyrate 
• 74288-39-4 (3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one 
• 98391-92-5 3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone 
• 101067-94-1 Benzoic acid (R)-1-{(2R,3S)-2-[3-diazo-3-(4-nitro-benzyloxycarbonyl)-2-oxo-propyl]-4-oxo-azetidin-3-yl}-ethyl ester 
• 98269-71-7 1-(tert-butyldimethylsilyl)-3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone 
• 98269-63-7 3-<(E)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone 
• 83997-55-1 (3R,4R)-3-ethyl-4-<3-diazo-2-oxo-3-<<(p-nitrobenzyl)oxy>carbonyl>propyl>-2-azetidinone 

Relevant academic research and scientific papers

Efficient method for silylation of p-nitrobenzyl-2-diazoacetoacetate

An efficient new method for the silylation of p-nitrobenzyl-2- diazoacetoacetate using hexamethyl disilane and iodine is presented. Copyright Taylor & Francis LLC.

PROCESS FOR PREPARATION OF ESTERS OF 2-DIAZO-3-TRIMETHYLSILYLOXY-3-BUTENOIC ACID

The present invention relates to a process for the preparation of esters of 2-diazo-3-trimethylsilyloxy-3-butenoic acid which comprises reacting a diazoacetoacetate with iodotrimethylsilane in the presence of an organic base, wherein iodotrimethylsilane is prepared by reacting hexamethyldisilane with iodine. The present invention further relates to converting such esters of 2-diazo-3-trimethylsilyloxy-3-butenoic acid to other compounds, such as a substituted diazoazetidinone, an azetidinone, or a bicyclo ketoester.

Process for preparing an enol silyl ether compound

A process for preparing an enol silyl ether compound from a diazoacetoacetic acid ester having the general formula (IV): STR1 wherein R1 is a lower alkyl group having 1 to 6 carbon atoms, phenyl group, a substituted phenyl group, an aralkyl group or allyl group, and R2, R3 and R4 are the same or mutually different and each is a lower alkyl group having 1 to 6 carbon atoms, which comprises reacting a diazoacetoacetic acid ester having the general formula (I): STR2 wherein R1 is the same as defined above, with a trialkylsilyl chloride having the general formula (II): STR3 wherein R2, R3 and R4 are the same as defined above, in an inert solvent in the presence of an organic base and an alkali halide having the general formula (III): wherein M is an alkaline metal and X is bromine atom or iodine atom. The desired compound is useful as an intermediate for synthesis of carbapenem β-lactam antibiotics.

Carbapenem intermediates

A new process is provided for preparing the key carbapenem intermediates of the formula STR1 wherein R5 and R6 each independently represent hydrogen or methyl and R1 represents a conventional carboxyl-protecting group.

Useful Chemistry of 3-(1-Methylethylidene)-4-acetoxy-2-azetidinone: A Formal Synthesis of (+/-)-Asparenomycin C

3-(1-Methylethylidene)-4-acetoxy-2-azetidinone (5) was prepared from the addition of chlorosulfonyl isocyanate to 1-acetoxy-3-methylbuta-1,2-diene.Isolated as a stable crystalline solid, this material is a versatile intermediate and is used in a formal sy