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Regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols from conduritol B epoxide

Academic Article
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Overview

authors

  • Serrano-Navarro, Pedro
  • Llebaria, A.
  • Delgado, A.

publication date

  • September 2005

journal

  • Journal of Organic Chemistry  Journal

abstract

  • [Chemical reaction: See text] A systematic approach to the regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols arising from tetra-O-benzylconduritol B epoxide (9) and its aziridine analogue 22, respectively, is described. In all cases, the synthetic methodologies rely on the regio- and stereocontrolled azidolysis of the starting precursors to give the corresponding trans regioadducts. Subsequent functional group manipulation under strict configurational control affords the isomeric cis adducts. Chemoselective functionalization of the diamine moiety in 1,2-diaminoinositol derivatives can be achieved by the proper design of the reaction sequence and choice of reagents. The described protocols allow efficient access to each of the eight possible configurations of the 1,2-diamino and 1,2-amino alcohol moieties from chemical modifications of the epoxide moiety on the common precursor 9.

subject areas

  • Amines
  • Epoxy Compounds
  • Indicators and Reagents
  • Inositol
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo050521a

PubMed ID

  • 16277302
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Additional Document Info

start page

  • 7829

end page

  • 7840

volume

  • 70

issue

  • 20

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