Release of Ring Strain as Driving Force for Inversion of Stereochemistry - Application to the Synthesis of Ribopyranosides from Xylopyranosides
Författare
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.
Avdelning/ar
Publiceringsår
2014
Språk
Engelska
Sidor
1271-1274
Publikation/Tidskrift/Serie
Synlett
Volym
25
Issue
9
Dokumenttyp
Artikel i tidskrift
Förlag
Georg Thieme Verlag
Ämne
- Chemical Sciences
Nyckelord
- acetals
- carbohydrates
- isomerization
- ring strain
- stereoselective
- synthesis
Status
Published
ISBN/ISSN/Övrigt
- ISSN: 0936-5214