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


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 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    R. J. Ferrier and S. Middleton, Chem. Rev., 1993, 93, 2779.CrossRefGoogle Scholar
  2. 2.
    N. K. Kochetkov, A. F. Sviridov, M. S. Ermolenko, D. V. Yashunskii, and O. S. Chizhov, Uglevody v sinteze prirodnykh soedinenii [Carbohydrates in Synthesis of Natural Compounds], Nauka, Moscow, 1984, 288 pp. (in Russian).Google Scholar
  3. 3.
    Y. H. Jin and C. K. Chu, Tetrahedron Lett., 2002, 43, 414.Google Scholar
  4. 4.
    H. R. Moon, W. J. Choi, H. O. Kim, L. S. Jeong, V. H. Jin, and C. K. Chu, Tetrahedron Asymmetry, 2002, 13, 1189.CrossRefGoogle Scholar
  5. 5.
    P. Belanger and P. Prasit, Tetrahedron Lett., 1988, 29, 5521.CrossRefGoogle Scholar
  6. 6.
    A. Martinez-Grau and J. Marco-Contelles, Chem. Soc. Rev., 1998, 27, 155.Google Scholar
  7. 7.
    A. Chenede, P. Pothier, M. Sollogoub, A. J. Fairbans, and P. Sinay, J. Chem. Soc., Chem. Commun., 1995, 1373.Google Scholar
  8. 8.
    J. M. Hill, E. J. Hutchinson, D. M. Le Grand, and S. M. Roberts, J. Chem. Soc., Perkin Trans. 1, 1994, 1483.Google Scholar
  9. 9.
    R. V. Bikbulatov, F. A. Akbutina, L. V. Spirikhin, and M. S. Miftakhov, Mendeleev Commun., 2003, 3, 153.Google Scholar
  10. 10.
    E. V. Carstensen, H. I. Duyustee, G. A. Van der Marel, J. H. Van Boom, J. Nielsen, H. S. Overklee, and M. Overhand, J. Carbohydr. Chem., 2003, 22, 241.CrossRefGoogle Scholar
  11. 11.
    S. M. Ali, K. Ramesh, and R. T. Borhart, Tetrahedron Lett., 1990, 31, 1509.Google Scholar
  12. 12.
    J. P. H. Verheyden, A. C. Richardson, R. S. Bhatt, B. D. Grant, W. L. Fitch, and J. G. Moffatt, Pure Appl. Chem., 1978, 30, 1363.Google Scholar
  13. 13.
    Thin-Layer Chromatography, Ed. J. G. Kirchner, 1, Wiley, New York, 1978.Google Scholar

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

Personalised recommendations