The browser you are using is not supported by this website. All versions of Internet Explorer are no longer supported, either by us or Microsoft (read more here: https://www.microsoft.com/en-us/microsoft-365/windows/end-of-ie-support).

Please use a modern browser to fully experience our website, such as the newest versions of Edge, Chrome, Firefox or Safari etc.

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

På svenska

Author

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.

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