Sophie Manner
Director of studies
Release of Ring Strain as Driving Force for Inversion of Stereochemistry - Application to the Synthesis of Ribopyranosides from Xylopyranosides
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.
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