Stereoselective synthesis of C-glycosylphosphonates from their ketols. Reconsideration of an abandoned route

Alessandro Dondoni; Alberto Marra; Claudia Pasti

doi:10.1016/S0957-4166(99)00477-2

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Stereoselective synthesis of C-glycosylphosphonates from their ketols. Reconsideration of an abandoned route

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Stereoselective synthesis of C-glycosylphosphonates from their ketols. Reconsideration of an abandoned route

Alessandro Dondoni, Alberto Marra et Claudia Pasti

Tetrahedron: asymmetry, Vol.11(1), pp.305-317

28/01/2000

DOI: https://doi.org/10.1016/S0957-4166(99)00477-2

Résumé

Isosteric phosphonate analogues of glycosyl 1-phosphates have been obtained by addition of LiCH 2P(O)(OMe) 2 to glyconolactones followed by Et 3SiH–TMSOTf reductive dehydroxylation of the resultant ketols. The compounds prepared include four β-linked pyranose derivatives ( d- galacto, 2-azido-2-deoxy- d- galacto, d- gluco, d- manno) and one β-linked furanose derivative ( d- manno). In the latter case the ketol was activated as its 2-acetate. In agreement with an observation in another laboratory, the dehydroxylation of a model ketol phosphonate failed with the use of Et 3SiH–BF 3·Et 2O.

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Titre: Stereoselective synthesis of C-glycosylphosphonates from their ketols. Reconsideration of an abandoned route
Créateurs - sans rôle: Alessandro Dondoni
Alberto Marra
Claudia Pasti
Détails de publication: Tetrahedron: asymmetry, Vol.11(1), pp.305-317
Éditeur: Elsevier Ltd
Nombre de pages: 13
Identifiants: 99163244509311
Unité académique: Institut des Biomolécules Max Mousseron - IBMM
Langue: English
Type de ressource: Journal article