Monodisperse oligoethylene glycols (M-OEGs)-containing symmetrical secondary amines are highly valuable synthetic intermediates in drug development and materials sciences. Scalable three-step synthesis of M-OEGs secondary amines with flexible M-OEGs and/or alkyl...
The one-pot nucleophilic
ring-opening reaction of oligoethylene
glycol macrocyclic sulfates provides an efficient strategy for the
monofunctionalization of oligoethylene glycols without protecting
or activating group manipulation. In this strategy, the hydrolysis
process is generally promoted by sulfuric acid, which is hazardous,
difficult to handle, environmentally unfriendly, and unfit for industrial
operation. Here, we explored a convenient handling solid acid, Amberlyst-15,
as a replacement for sulfuric acid to accomplish the hydrolysis of
sulfate salt intermediates. With this method, 18 valuable oligoethylene
glycol derivatives were prepared with high efficiency, and gram-scale
applicability of this method has been successfully demonstrated to
afford a clickable oligoethylene glycol derivative 1b and a valuable building block 1g for F-19 magnetic
resonance imaging traceable biomaterial construction.
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