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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 (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
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
2014-07-16 15:45:07
date last changed
2017-01-01 06:23:36
@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},
  keyword      = {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},
  volume       = {25},
  year         = {2014},
}