A Short and Convenient Synthesis of closo-Dodecaborate Sugar Conjugates

Daniela Imperio, Barbara Muz, Abdel Kareem Azab, Silvia Fallarini, Grazia Lombardi, Luigi Panza

Research output: Contribution to journalArticle

1 Scopus citations

Abstract

Dodecaborate anions represent a suitable boron source for boron neutron capture therapy (BNCT). Sugar derivatives of dodecaborate have been prepared through the ring-opening reaction of cyclic oxonium ions by alkoxide nucleophiles. According to this general approach, a convenient and short synthesis of three derivatives of dodecaborate-sugar conjugates is herein reported. Glucose, galactose and fructose have been chosen for their expected preferential uptake by tumor cells compared to healthy cells. The free hydroxyl group of isopropylidene protected sugars was exploited as nucleophile to open a dodecaborate cyclic oxonium salt, giving products containing a spacer between the sugar and the boron cluster. Deprotection of the sugar moiety in acidic conditions gave the desired compounds in excellent yield.

Original languageEnglish
Pages (from-to)7228-7232
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number43
DOIs
StatePublished - Nov 24 2019

Keywords

  • BNCT
  • Boron
  • Dodecaborates
  • Drug delivery
  • Sugars

Fingerprint Dive into the research topics of 'A Short and Convenient Synthesis of closo-Dodecaborate Sugar Conjugates'. Together they form a unique fingerprint.

  • Cite this