Synthesis of a water soluble boron neutron capture therapy agent: 1-amino-3-[2-(7-{3-[2-(2-hydroxymethyl-ethoxy)-1-(2-hydroxy-1-hydroxymethyl-ethoxymethyl)ethoxy]propyl}-1,7-di-carba-closo-dodecaboran-1-yl)ethyl]cyclobutanecarboxylic acid

Add time:07/13/2019    Source:sciencedirect.com

A water soluble boronated amino acid containing a cascade polyol, 1-amino-3-[2-(7-{3-[2-(2-hydroxymethyl-ethoxy)-1-(2-hydroxy-1-hydroxymethyl-ethoxymethyl)ethoxy]propyl}-1,7-di-carba-closo-dodecaboran-1-yl)ethyl]cyclobutanecarboxylic acid, has been developed. The key step in the synthesis is the alkylation of 3-[2-(1,7-dicarba-closo-dodecarboran-1-yl)ethyl]cyclobutanone hemithioketal with toluene-4-sulfonic acid 3-[2-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-1-(2-benzyloxy-1-benzyloxymethyl-ethoxymethyl)ethoxy]propyl ester which gave the required precursor ketone which was then converted to the title amino acid via a Bücherer–Strecker synthesis followed by hydrogenolysis to remove the benzyl protecting groups.

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