170148-26-2

Upstream product

• 420-37-1 trimethoxonium tetrafluoroborate 
• 132974-83-5 (5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 17342-08-4 (S)-Pyroglutaminol 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 170421-37-1 Amino-[(S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester 
• 1207721-49-0 C₄₃H₄₉N₃O₄Si 

Relevant academic research and scientific papers

Approach to Fully Substituted Cyclic Nitrones from N-Hydroxylactam Derivatives: Development and Application to the Total Synthesis of Cylindricine C

An approach to cyclic nitrones from N-hydroxylactam derivatives is documented. The nucleophilic addition of an organolithium reagent to an N-OSEM [SEM=2-(trimethylsilyl)ethoxymethyl] lactam forms a five-membered chelated intermediate, which undergoes both elimination and deprotection to give a fully substituted nitrone in a one-pot process. When combined with the N-oxidation of easily available chiral lactams, this method becomes especially useful for the quick synthesis of chiral nitrones in enantio-pure form, enabling the concise total synthesis of cylindricine C.

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 Property, and Cytotoxicity of the Carzinophilin Congeners Carrying a 2-(1-Acylamino-1-alkoxycarbonyl)methylidene-1-azabicyclohexane System

Synthesis of the title compounds was achieved by employing condensation of the 2-methoxy-1-pyrroline with ethyl nitroacetate and construction of 1-azabicyclohexane systems from 5-mesyloxymethylpirrolidines as key steps.Some of these congeners which carry a C6-C11 unit involving the naphthalene part, were found to exhibit prominent cytotoxicity and effectively alkylate nucleophiles at both the aziridine and epoxide moieties. Key words: carzinophilin congeners, synthesis, chemical property, reaction with nucleophiles, cytotoxicity