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Título: | Enantiodivergent synthesis of d- and l-erythro-sphingosines through mannich-type reactions of N-benzyl-2,3-O-isopropylidene-d-glyceraldehyde nitrone |
Autor: | Merino, Pedro CSIC ORCID ; Jiménez, Pablo CSIC ORCID; Tejero, Tomás CSIC ORCID | Fecha de publicación: | may-2006 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 71(12): 4685-4688 (2006) | Resumen: | The addition of a 2-silyloxy silylketene acetal to N-benzyl-2,3-O-isopropylidene-d-glyceraldehyde nitrone (Mannich-type reaction) can be stereocontrolled to give 2S,3S,4S and 2R,3R,4S adducts as major compounds, depending on whether the reaction is activated with zinc(II) triflate or tin(IV) chloride, respectively. The corresponding major adducts were used for preparing diastereomeric polyhydroxy-β-aminoesters that were further converted into suitable orthogonally protected enantiomeric d- and l-erythro-sphingosines. | Descripción: | 4 pages, 2 schemes, 1 table.-- Supporting Information Available: http://pubs.acs.org. | Versión del editor: | http://dx.doi.org/10.1021/jo060465t | URI: | http://hdl.handle.net/10261/19592 | DOI: | 10.1021/jo060465t | ISSN: | 0022-3263 |
Aparece en las colecciones: | (ICMA) Artículos |
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