Release of Ring Strain as Driving Force for Inversion of Stereochemistry - Application to the Synthesis of Ribopyranosides from Xylopyranosides
(2014) In Synlett 25(9). p.1271-1274- 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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/4545004
- author
- Manner, Sophie LU and Ellervik, Ulf LU
- organization
- publishing date
- 2014
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- acetals, carbohydrates, isomerization, ring strain, stereoselective, synthesis
- in
- Synlett
- volume
- 25
- issue
- 9
- pages
- 1271 - 1274
- publisher
- Georg Thieme Verlag
- external identifiers
-
- wos:000337238300011
- scopus:84901635179
- ISSN
- 0936-5214
- DOI
- 10.1055/s-0033-1341203
- language
- English
- LU publication?
- yes
- id
- 5fb0f501-d2c9-45ef-a183-c6596b425543 (old id 4545004)
- date added to LUP
- 2016-04-01 14:42:18
- date last changed
- 2024-05-09 03:52:27
@article{5fb0f501-d2c9-45ef-a183-c6596b425543, 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.}}, author = {{Manner, Sophie and Ellervik, Ulf}}, issn = {{0936-5214}}, keywords = {{acetals; carbohydrates; isomerization; ring strain; stereoselective; synthesis}}, language = {{eng}}, number = {{9}}, pages = {{1271--1274}}, publisher = {{Georg Thieme Verlag}}, series = {{Synlett}}, title = {{Release of Ring Strain as Driving Force for Inversion of Stereochemistry - Application to the Synthesis of Ribopyranosides from Xylopyranosides}}, url = {{http://dx.doi.org/10.1055/s-0033-1341203}}, doi = {{10.1055/s-0033-1341203}}, volume = {{25}}, year = {{2014}}, }