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 |
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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 |