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

Bhaskar C. Das, George Kabalka, Rajiv R. Srivastava, Weiliang Bao, Sasmita Das, Guisheng Li

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)255-261
Number of pages7
JournalJournal of Organometallic Chemistry
Volume614
Issue number615
DOIs
StatePublished - Dec 8 2000

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Boron Neutron Capture Therapy
Boron
amino acids
Amino acids
therapy
Neutrons
boron
Amino Acids
neutrons
hydrogenolysis
Hydrogenolysis
acids
Acids
Sulfonic Acids
Water
sulfonic acid
Polyols
alkylation
Alkylation
Toluene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

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title = "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",
abstract = "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 B{\"u}cherer-Strecker synthesis followed by hydrogenolysis to remove the benzyl protecting groups.",
author = "Das, {Bhaskar C.} and George Kabalka and Srivastava, {Rajiv R.} and Weiliang Bao and Sasmita Das and Guisheng Li",
year = "2000",
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T1 - Synthesis of a water soluble boron neutron capture therapy agent

T2 - 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

AU - Das, Bhaskar C.

AU - Kabalka, George

AU - Srivastava, Rajiv R.

AU - Bao, Weiliang

AU - Das, Sasmita

AU - Li, Guisheng

PY - 2000/12/8

Y1 - 2000/12/8

N2 - 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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