142890-16-2

Upstream product

• 65100-24-5 dibenzyl 2-bromomalonate 
• 142890-13-9 (S)-5-[(tert-butyl)-diphenylsilyloxy-methyl]-2-thiopyrrolidinone 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 17342-08-4 (S)-Pyroglutaminol 
• 132974-83-5 (5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one 

Downstream Products

• 153649-64-0 2-((S)-5-Hydroxymethyl-pyrrolidin-2-ylidene)-malonic acid dibenzyl ester 
• 142890-20-8 2-[(S)-5-(Toluene-4-sulfonyloxymethyl)-pyrrolidin-2-ylidene]-malonic acid dibenzyl ester 
• 142890-26-4 2-((S)-5-Iodomethyl-pyrrolidin-2-ylidene)-malonic acid dibenzyl ester 
• 142890-24-2 2-((S)-5-Bromomethyl-pyrrolidin-2-ylidene)-malonic acid dibenzyl ester 
• 142890-29-7 (S)-2-(1-Aza-bicyclo[3.1.0]hex-2-ylidene)-malonic acid dibenzyl ester 

Relevant academic research and scientific papers

Synthetic studies of carzinophilin. Part 1: Synthesis of 2-methylidene-1-azabicyclo[3.1.0]hexane systems related to carzinophilin

Synthesis of the model compounds of carzinophilin carrying 2-methylidene-1-aza-bicyclo[3.1.0]hexane systems was achieved. Formation of malonylidenes or N-acyl-glycinylidenepyrrolidines was carried out by utilizing Eschenmoser's sulfide contraction or Herdeis's condensation between the 2-methylthio-Δ1-pyrrolone derivatives and ethyl nitroacetate, respectively. The 1-azabicyclo-[3.1.0]hexane systems were constructed by base-promoted aziridine formation.

Synthesis, Chemical Reactivity, and Cytotoxicity of 2-Bis(alkoxycarbonyl)methyliden-1-azabicyclohexane Systems Related to Antitumor Antibiotic Carzinophilin A

Enantiomeric pairs of the title compounds were synthesized starting from (S)- and (R)-pyroglutamic acid.They were found to be susceptible to nucleophilic ring opening of aziridine moieties and to exhibit weak in vitro cytotoxicity.