79975-81-8

Upstream product

• 20485-44-3 2,3-dimethyl-2,3-diaminobutane 
• 52267-51-3 benzyl diazoacetate 
• 75-77-4 chloro-trimethyl-silane 
• 52267-50-2 benzyl-α-diazo-acetoacetate 

Downstream Products

• 79975-82-9 2-Diazo-4-[(2R,3S)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid benzyl ester 
• 79975-86-3 (2R,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 79975-87-4 4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-diazo-3-oxo-butyric acid benzyl ester 
• 74476-29-2 4-(3-benzyloxycarbonyl-3-diazo-2-oxopropyl)-azetidin-2-one 

Relevant academic research and scientific papers

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.

Stereospecific synthesis of thienamycin from penicillin

A stereospecific conversion of penicillin to thienamycin, using diisopropylamine borane and magnesium trifluoroacetate to prepare the hydroxyethyl side chain and acetoacetate dianion equivalent disilylethyl to prepare the β-ketoester side chain.