344550-02-3

Upstream product

• 108-24-7 acetic anhydride 
• 344549-99-1 20-acetyl-2'-O-(tert-butyldimethylsilyl)-4-deacetyl-5,6-dehydro-7-oxo-5-O-secopaclitaxel 

Downstream Products

• 344550-11-4 benzoic acid 4,10-diacetoxy-4-acetoxymethyl-13-[3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7-methylsulfanylthiocarboxyoxy-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester 
• 344550-12-5 Benzoic acid (1S,2S,3R,4S,7S,8S,10R,13S)-4,10-diacetoxy-4-acetoxymethyl-13-[(2R,3S)-3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1,7-dihydroxy-8,12,15,15-tetramethyl-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester 
• 344550-09-0 Benzoic acid (1S,2S,3R,4S,7R,8S,10R,13S)-4,10-diacetoxy-4-acetoxymethyl-13-[(2R,3S)-3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1,7-dihydroxy-8,12,15,15-tetramethyl-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester 

Relevant academic research and scientific papers

Novel D-seco paclitaxel analogues: Synthesis, biological evaluation, and model testing

Four new D-secopaclitaxel analogues were synthesized from paclitaxel. The key step of the synthesis involved the opening of the D-ring by Jones oxidation. Two of the compounds had been predicted to be nearly as active as paclitaxel in a minireceptor model of the binding site on tubulin, but all were biologically inactive in an in vitro cytotoxic assay and a tubulin assembly assay. The biological results identify a weakness in our predictive minireceptor model and suggest a corrective remedy in which additional amino acids are needed to accommodate ligand-protein steric effects around the oxetane ring. These changes to the model lead to correct predictions of the bioactivity. Conformational analysis and dynamics simulations of the compounds showed that the 4-acetyl substituent is as important as the oxetane in determining the A ring conformation.