Carbohydrate-2-deoxy-2-phosphonates : simple synthesis and Horner-Emmons reaction
- 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.
| Author details: | Elangovan ElamparuthiGND, Torsten LinkerORCiDGND |
|---|---|
| URL: | http://onlinelibrary.wiley.com/journal/10.1002/(28ISSN)291521-3773 |
| DOI: | https://doi.org/10.1002/anie.200804725 |
| ISSN: | 1433-7851 |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2009 |
| Publication year: | 2009 |
| Release date: | 2017/03/25 |
| Source: | Angewandte Chemie : international edition. - ISSN 1433-7851. - 48 (2009), 10, S. 1853 - 1855 |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
