Skip to main content
SpringerLink
Log in

Stereoelectronic control of cleavage of dioxolane five-membered ring on carbohydrates

  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

A mechanism about the origin of the selectivities for the cleavage of dioxolane five-membered rings on pyranoside rings was suggested. Quantum chemical studies were performed to testify the rationality of the mechanism. It is thus suggested that the selectivities should be dependent on the differences of the free energy at the transition states when the five-membered ring cleaves. Natural bond orbital(NBO) analysis was further made to assess the influence of stereoelectronic effects on the selectivities.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Binkley R. W., Goewey G. S., Johnston J. C., J. Org. Chem., 1984, 49(6), 992

    Article  CAS  Google Scholar 

  2. Deslongchamps P., Tetrahedron, 1975, 31(20), 2463

    Article  CAS  Google Scholar 

  3. King J. F., Allbutt A. D., Can. J. Chem., 1970, 48(11), 1754

    Article  CAS  Google Scholar 

  4. Deslongchamps P., Chênevert R., Taillefer R. J., Moreau C., Saunders J. K., Can. J. Chem., 1975, 53(11), 1601

    Article  CAS  Google Scholar 

  5. Dong H., Pei Z. C., Ramström O., Chem. Commun., 2008, 1359

    Google Scholar 

  6. Dong H., Pei Z. C., Ramström O., J. Org. Chem., 2006, 71(8), 3306

    Article  CAS  Google Scholar 

  7. Dong H., Pei Z. C., Angelin M., Byström S., Ramström O., J. Org. Chem., 2007, 72(10), 3694

    Article  CAS  Google Scholar 

  8. Binkley R. W., J. Org. Chem., 1991, 56(12), 3892

    Article  CAS  Google Scholar 

  9. Deng S. L., Gangadharmath U., Chang C. W. T., J. Org. Chem., 2006, 71(14), 5179

    Article  CAS  Google Scholar 

  10. Deng S. L., Chang C. W. T., Synlett., 2006, 756

    Google Scholar 

  11. Chittenden G. J. F., Buchanan J. G., Carbohydr. Res., 1969, 11(3), 379

    Article  CAS  Google Scholar 

  12. Perrin C. L., Acc. Chem. Res., 2002, 35(1), 28

    Article  CAS  Google Scholar 

  13. Knapp S., Kukkola P. J., Sharma S., Dhar T. G. M., Naughton A. B. J., J. Org. Chem., 1990, 55(22), 5700

    Article  CAS  Google Scholar 

  14. Knapp S., Naughton A. B. J., Jaramillo C., Pipik B., J. Org. Chem., 1992, 57(26), 7328

    Article  CAS  Google Scholar 

  15. Wang H. S., She J., Zhang L. H., Ye X. S., J. Org. Chem., 2004, 69(17), 5774

    Article  CAS  Google Scholar 

  16. Hu G. X., Vasella A., Helv. Chim. Acta, 2002, 85(12), 4369

    Article  CAS  Google Scholar 

  17. Carey F. A., Sundberg R. J., Advanced Organic Chemistry, Kluwer Academic/Plenum Publishers, New York, 2000, 157

    Google Scholar 

  18. Ding X. Q., Ding J. J., Li D. Y., Sun Y., Chen J. S., Chem. J. Chinese Universities, 2012, 33(5), 1063

    CAS  Google Scholar 

  19. Sang Y. M., Yan L. K., Wen S. Z., Cong S., Su Z. M., Chem. J. Chinese Universities, 2012, 33(6), 1285

    CAS  Google Scholar 

  20. Wan S. Q., Zhang Y., Zhang H., Sun C. C., Chem. J. Chinese Universities, 2012, 33(7), 1505

    CAS  Google Scholar 

  21. Wang Y., Zhang P., Yang K., Hou Y. M., Chem. J. Chinese Universities, 2012, 33(8), 1799

    CAS  Google Scholar 

  22. Liu N. N., Ding Y. H., Chem. J. Chinese Universities, 2012, 33(9), 2043

    CAS  Google Scholar 

  23. Fan L. T., Li Y., Wu D., Li Z. R., Sun C. C., Chem. J. Chinese Universities, 2012, 33(10), 2320

    CAS  Google Scholar 

  24. Chai J. D., Head-Gordon M., Phys. Chem. Chem. Phys., 2008, 10(44), 6615

    Article  CAS  Google Scholar 

  25. Cossi M., Rega N., Scalmani G., Barone V., J. Comp. Chem., 2003, 24(6), 669

    Article  CAS  Google Scholar 

  26. Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Mennucci B., Petersson G. A., Nakatsuji H., Caricato M., Li X., Hratchian H. P., Izmaylov A. F., Bloino J., Zheng G., Sonnenberg J. L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J. A. Jr., Peralta J. E., Ogliaro F., Bearpark M., Heyd J. J., Brothers E., Kudin K. N., Staroverov V. N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J. C., Iyengar S. S., Tomasi J., Cossi M., Rega N., Millam N. J., Klene M., Knox J. E., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Martin R. L., Morokuma K., Zakrzewski V. G., Voth G. A., Salvador P., Dannenberg J. J., Dapprich S., Daniels A. D., Farkas Ö., Foresman J. B., Ortiz J. V., Cioslowski J., Fox D. J., Gaussian 09, Revision C.01, Gaussian Inc., Wallingford CT, 2009

    Google Scholar 

  27. Glendening E. D., Reed A. E., Carpenter J. E., Weinhold F., NBO 3.1, Theoretical Chemistry Institute, University of Wisconsin, Madison WI, 2001

    Google Scholar 

  28. Alabugin I. V., Manoharan M., Zeidan T. A., J. Am. Chem. Soc., 2003, 125(46), 14014

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun, 130021, P. R. China

    Xiao-liang Pan, Wei Liu & Jing-yao Liu

  2. School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, 430074, P. R. China

    Yi-xuan Zhou & Hai Dong

Authors
  1. Xiao-liang Pan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yi-xuan Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wei Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jing-yao Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hai Dong
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Jing-yao Liu or Hai Dong.

Additional information

Supported by the National Natural Science Foundation of China(No.20973077), the Program for New Century Excellent Talents in University of China(No.NCET-07-0358) and the Brain Gain Fund of Huazhong University of Science and Technology, China.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pan, Xl., Zhou, Yx., Liu, W. et al. Stereoelectronic control of cleavage of dioxolane five-membered ring on carbohydrates. Chem. Res. Chin. Univ. 29, 551–555 (2013). https://doi.org/10.1007/s40242-013-2293-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-013-2293-6

Keywords

Search

Navigation