Synlett 2014; 25(09): 1271-1274
DOI: 10.1055/s-0033-1341203
letter
© Georg Thieme Verlag Stuttgart · New York

Release of Ring Strain as Driving Force for Inversion of Stereochemistry – Application to the Synthesis of Ribopyranosides from Xylopyranosides

Sophie Manner
Center for Analysis and Synthesis, Center for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, 221 00 Lund, Sweden   Fax: +46(46)2228209   Email: ulf.ellervik@chem.lu.se
,
Ulf Ellervik*
Center for Analysis and Synthesis, Center for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, 221 00 Lund, Sweden   Fax: +46(46)2228209   Email: ulf.ellervik@chem.lu.se
› Author Affiliations
Further Information

Publication History

Received: 24 February 2014

Accepted after revision: 21 March 2014

Publication Date:
30 April 2014 (online)

Abstract

By using a Swern oxidation–epimerization–reduction ­sequence it is possible to selectively epimerize any position in isopropylidene-protected xylopyranosides, thus forming arabinosides, ribosides, and lyxosides. The driving force for epimerization of position 3 (xylo to ribo) is the release of ring strain by going from a 1,2-trans-acetal to a 1,2-cis-acetal.

Supporting Information

 
  • References

    • 1a Kondo Y. Carbohydr. Res. 1982; 110: 339
    • 1b Kishimoto T, Ikeda T, Karlsson O, Magara K, Hosoya S. J. Wood Sci. 2002; 48: 32
  • 2 Siegbahn A, Aili U, Ochocinska A, Olofsson M, Rönnols J, Mani K, Widmalm G, Ellervik U. Bioorg. Med. Chem. 2011; 19: 4114
  • 3 Greene TW, Wuts PG. M. Protective Groups in Organic Synthesis. John Wiley and Sons; New York: 1999: 207
  • 4 Catelani G, Colonna F, Marra A. Carbohydr. Res. 1988; 182: 297
  • 5 Tojo G, Fernandez M. Oxidations of Alcohols to Aldehydes and Ketones . Springer; Heidelberg: 2006: 153
  • 6 Spartan ’10, Version 1.1.0; Wavefunction, Inc.: Irvine (CA, USA).
  • 7 Ohlinger WS, Klunzinger PE, Deppmeier BJ, Hehre WJ. J. Phys. Chem. A 2009; 113: 2165
  • 8 Anderson JE, Ijeh AI. J. Chem. Soc., Perkin Trans. 2 1994; 1965