Synthesis of all possible regioisomers of scyllo-inositol phosphate

Sung Kee Chung, Yong Uk Kwon, Young Tae Chang, Kwang Hoon Sohn, Jung Han Shin, Kyu Hwan Park, Bong Jin Hong, In Hee Chung

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25 Scopus citations

Abstract

scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All possible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into scyllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis- diol. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo- IP(n). (C) 1999 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)2577-2589
Number of pages13
JournalBioorganic and Medicinal Chemistry
Volume7
Issue number11
DOIs
StatePublished - Nov 1999

Keywords

  • Benzoyl migration
  • Inositol phosphates
  • Mitsunobu reaction
  • scyllo-Inositol

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