Synthesis of Methoxy-Substituted Exocyclic (E)- and (Z)-Unsaturated Methyl Pyranosides and a Study of Their Reactivity towards Lewis Acids

✍ Scribed by Aurélie Deleuze; Matthieu Sollogoub; Yves Blériot; Jérôme Marrot; Pierre Sinaÿ

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 154 KB
• Volume: 2003
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200300105

✦ Synopsis

Abstract

The first synthesis of methoxy‐substituted exocyclic (E)‐ and (Z)‐unsaturated methyl pyranosides is reported involving the syn elimination of a selenoxide derivative as a key step. The rearrangement of these exocyclic enol ethers in the presence of TIBAL and DIBAL‐H is also described. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)