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Sophie Manner

Director of studies

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

Author

  • Sophie Manner
  • Ulf Ellervik

Summary, in English

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.

Department/s

  • Centre for Analysis and Synthesis

Publishing year

2014

Language

English

Pages

1271-1274

Publication/Series

Synlett

Volume

25

Issue

9

Document type

Journal article

Publisher

Georg Thieme Verlag

Topic

  • Chemical Sciences

Keywords

  • acetals
  • carbohydrates
  • isomerization
  • ring strain
  • stereoselective
  • synthesis

Status

Published

ISBN/ISSN/Other

  • ISSN: 0936-5214