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

Manner, Sophie LU and Ellervik, Ulf LU orcid (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.
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author
and
organization
publishing date
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
2025-10-14 09:17:38
@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}},
}