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

Authors

  • 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
Weitere Informationen

Publikationsverlauf

Received: 24. Februar 2014

Accepted after revision: 21. März 2014

Publikationsdatum:
30. April 2014 (online)


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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