This research was generously supported by the Deutsche Forschungsgemeinschaft (Li 556/7-3).
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Communication
Carbohydrate-2-deoxy-2-phosphonates: Simple Synthesis and Horner–Emmons Reaction†
Article first published online: 23 JAN 2009
DOI: 10.1002/anie.200804725
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 48, Issue 10, pages 1853–1855, February 23, 2009
Additional Information
How to Cite
Elamparuthi, E. and Linker, T. (2009), Carbohydrate-2-deoxy-2-phosphonates: Simple Synthesis and Horner–Emmons Reaction. Angew. Chem. Int. Ed., 48: 1853–1855. doi: 10.1002/anie.200804725
- †
Publication History
- Issue published online: 17 FEB 2009
- Article first published online: 23 JAN 2009
- Manuscript Revised: 2 DEC 2008
- Manuscript Received: 26 SEP 2008
Funded by
- Deutsche Forschungsgemeinschaft. Grant Number: Li 556/7-3
Keywords:
- C
![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
C coupling; - carbohydrates;
- phosphorus;
- radical reactions;
- synthetic methods
Abstract
Phosphorus meets carbohydrates: Dimethyl phosphite reacts with ceric(IV) ammonium nitrate (CAN) to give phosphonyl radicals that add to glycals 1. The derivatives 2 were isolated in high yields and during a subsequent Horner–Emmons reaction underwent an interesting elimination to give 3,6-dihydro-2H-pyrans 3. The short sequence with simple precursors is applicable to the transformation of hexoses, pentoses, and disaccharides. Bn=benzyl.