355010-33-2

Upstream product

• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 355010-40-1 2-methylamino-4-nitrophenyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosiduronic acid 
• 355010-32-1 2-methylamino-4-nitrophenyl-β-D-glucopyranosiduronic acid 
• 191352-30-4 (2S,3S,4S,5R,6S)-2-(methoxycarbonyl)-6-(2-(methylamino)-4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 355010-34-3 2-(trimethylsilyl)ethyl [2-(N-chloroformyl-N-methylamino)-4-nitrophenyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside]uronate 

Relevant academic research and scientific papers

Cancer chemotherapy: A paclitaxel prodrug for ADEPT (Antibody-Directed Enzyme Prodrug Therapy)

A glucuronide-based prodrug of paclitaxel (taxol) has been synthesized for use in antibody-directed enzyme prodrug therapy (ADEPT). This three-component prodrug was obtained by coupling a glucuronyl derivative of N-methylamino 4-nitrophenol (10) to the 2′-hydroxy group of the side-chain of paclitaxel through an aromatic carbamate. Once deprotected, prodrug 2 was shown to be relatively stable in human serum, and to be significantly less cytotoxic (IC50 = 65 μM and 90 nM, respectively) than the parent drug. As expected, compound 2 efficiently releases taxol in the presence of β-glucuronidase.