First synthesis of P-aryl-phosphinosugars, organophosphorus analogues of C-arylglycosides

• Published in: Tetrahedron letters Vol. 46; no. 21; pp. 3741 - 3744
• Main Authors: Cristau, Henri-Jean, Monbrun, Jérôme, Schleiss, Julie, Virieux, David, Pirat, Jean-Luc
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 23.05.2005; Elsevier
• Subjects: Arylphosphinic; Chemical Sciences; Chemistry; Chemistry, Organic; Organic chemistry; Phostone; Physical Sciences; Polyhydroxylated; Science & Technology; Sugar analogues; Sugar analogues; Phostone; Arylphosphinic; Polyhydroxylated; polyhydroxylated; CYCLIC PHOSPHONATE ANALOGS; sugar analogues; arylphosphinic; INHIBITORS; DERIVATIVES; phostone; STRUCTURE-BASED DESIGN
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2005.03.148

The synthesis of the first example of P-arylphosphinosugar is reported. The protected polyhydroxylated 1,2-oxaphosphinane is prepared by a two steps sequence (phenylphosphinate addition on protected mannofuranose followed by intramolecular transesterification) on gram scale. Deprotection of the di-isopropylidene derivative using acidic cation-exchange resin affords the free hydroxy organophosphorus heterocycle analogous to C-arylglycosides. The synthesis and X-ray crystal structure of the first example of arylphosphinosugar are reported. The protected polyhydroxylated 1,2-oxaphosphinane is prepared by a two steps sequence (phenylphosphinate addition on protected mannofuranose followed by intramolecular transesterification) on gram scale. Deprotection of the di-isopropylidene derivative using acidic cation-exchange resin affords the free hydroxy organophosphorus heterocycle analogous to C-arylglycosides.