β-Rhamnosides from 6-thio mannosides.
| Autor: | Christina AE; Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands., van der Es D, Dinkelaar J, Overkleeft HS, van der Marel GA, Codée JD |
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| Jazyk: | angličtina |
| Zdroj: | Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2012 Mar 11; Vol. 48 (21), pp. 2686-8. Date of Electronic Publication: 2012 Feb 03. |
| DOI: | 10.1039/c2cc17623h |
| Abstrakt: | Upon condensation of 6-thio-6-deoxy-mannosyl donors 1,2-cis products are obtained with a high degree of stereoselectivity. Subsequent reductive removal of the 6-thio functionality gives 1,2-cis rhamnosides. The 1,2-cis-selectivity can be rationalized with a product forming (3)H(4)-oxocarbenium, which is in equilibrium with a bridged sulfonium intermediate. (This journal is © The Royal Society of Chemistry 2012) |
| Databáze: | MEDLINE |
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