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Russian Chemical Bulletin

, Volume 54, Issue 11, pp 2698–2701 | Cite as

Unexpected transformation of methyl 3,6-anhydro-2,7-dideoxy-7-iodo-4,5-O-isopropylidene-D-allo-heptonate in the dehydroiodination reaction with 1,8-diazabicyclo[5.4.0]undec-7-ene

  • N. A. Ivanova
  • Z. R. Valiullina
  • O. V. Shitikova
  • M. S. Miftakhov
Article

Abstract

The reaction of methyl 3,6-anhydro-2,7-dideoxy-7-iodo-4,5-O-isopropylidene-D-allo-heptonate with 1,8-diazabicyclo[5.4.0]undec-7-ene affords methyl 3,6-anhydro-2,7-dideoxy-4,5-O-isopropylidene-D-ribo-hept-6-enonate, which undergoes the previously unknown rearrangement into a 2,2-dimethyl-1,3-dioxole derivative.

Key words

2,3-O-isopropylidene-D-ribose olefination dehydroiodination rearrangement 

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Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • N. A. Ivanova
    • 1
  • Z. R. Valiullina
    • 1
  • O. V. Shitikova
    • 1
  • M. S. Miftakhov
    • 1
  1. 1.Institute of Organic ChemistryUfa Scientific Center of the Russian Academy of SciencesUfaRussian Federation

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