144318-33-2

Upstream product

• 22539-93-1 3-benzyloxypropanone 
• 100-51-6 benzyl alcohol 
• 4039-82-1 Benzyl propargyl ether 

Downstream Products

• 144318-34-3 N-(3-Benzyloxy-2-oxo-propyl)-N-(2-bromo-phenyl)-4-methyl-benzenesulfonamide 
• 131121-30-7 <α-(benzyloxy)acetyl>methylenetriphenylphosphorane 
• 849432-99-1 C₂₈H₃₀BrNO₅ 
• 144318-36-5 3-Benzyloxymethyl-3-(tetrahydro-pyran-2-yloxymethyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole 
• 144318-37-6 [3-Benzyloxymethyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-3-yl]-methanol 
• 475681-42-6 4-(4-benzyloxy-3-oxo-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 144318-41-2 4-(benzyloxy)-N-(3'-(benzyloxy)propan-2'-one)-1-bromo-N-tosyl-3-naphthylamine 

Relevant academic research and scientific papers

Enantioselective synthesis of the excitatory amino acid (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid

An enantioselective synthesis of the α,α-dialkyl-α-amino acid (1S,3R)-ACPD has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The ketone cyclization precursor was synthesized from Garner's aldehyde in high yield via a Wittig homologation and subsequent catalytic hydrogenation. Treatment of the ketone with 1.2 equiv of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the corresponding cyclopentene-containing CH-insertion product in 62-69% yield in high enantiomeric excess. Subsequent functional group manipulation allowed the synthesis of the amino acid (1S,3R)-ACPD to be completed.

Functional analogs of CC-1065 and the duocarmycins incorporating the 9a-(chloromethyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (C2BI) alkylation subunit: Synthesis and preliminary DNA alkylation studies

A concise and effective nine to ten step synthesis of 9a-(chloromethyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (C2BI) is detailed based on the implementation of a key 5-exo-trig aryl radical-alkene cyclization for direct introduction of a selectively protected 3,3-bis(hydroxymethyl)indoline. The incorporation of C2BI into functional analogs of CC-1065 and the duocarmycins (C2BI-COPI1, C2BI-CDPI2, C2BI-TMI, and C2BI-indole2) is described. The fundamental solvolytic behavior of N-BOC-C2BI is detailed (t1/2 = 433 h, pH = 3) in studies which reveal that the agent is approximately 12 times more stable than the authentic alkylation subunit of CC-1065 and that it participates in the stereoelectronically-controlled reaction with nucleophilic addition to the least substituted cyclopropane carbon. Preliminary studies demonstrating the DNA alkylation and cross-linking properties of C2BI-CDPI2 are presented.