RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2014; 25(09): 1271-1274
DOI: 10.1055/s-0033-1341203
DOI: 10.1055/s-0033-1341203
letter
Release of Ring Strain as Driving Force for Inversion of Stereochemistry – Application to the Synthesis of Ribopyranosides from Xylopyranosides
Weitere Informationen
Publikationsverlauf
Received: 24. Februar 2014
Accepted after revision: 21. März 2014
Publikationsdatum:
30. April 2014 (online)
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
- 1a Kondo Y. Carbohydr. Res. 1982; 110: 339
- 1b Kishimoto T, Ikeda T, Karlsson O, Magara K, Hosoya S. J. Wood Sci. 2002; 48: 32
- 2 Siegbahn A, Aili U, Ochocinska A, Olofsson M, Rönnols J, Mani K, Widmalm G, Ellervik U. Bioorg. Med. Chem. 2011; 19: 4114
- 3 Greene TW, Wuts PG. M. Protective Groups in Organic Synthesis. John Wiley and Sons; New York: 1999: 207
- 4 Catelani G, Colonna F, Marra A. Carbohydr. Res. 1988; 182: 297
- 5 Tojo G, Fernandez M. Oxidations of Alcohols to Aldehydes and Ketones . Springer; Heidelberg: 2006: 153
- 6 Spartan ’10, Version 1.1.0; Wavefunction, Inc.: Irvine (CA, USA).
- 7 Ohlinger WS, Klunzinger PE, Deppmeier BJ, Hehre WJ. J. Phys. Chem. A 2009; 113: 2165
- 8 Anderson JE, Ijeh AI. J. Chem. Soc., Perkin Trans. 2 1994; 1965