Tetrahedron

Synthesis of l-ascorbic acid derivatives as potential bone remodeling agents taking advantage of the Mitsunobu reaction

…, C Rubio, J Susperregui, L Latxague, G Déléris

Index: Vilaca, Gil; Rubio, Cyril; Susperregui, Jacques; Latxague, Laurent; Deleris, Gerard Tetrahedron, 2002 , vol. 58, # 45 p. 9249 - 9256

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Citation Number: 11

Abstract

The synthesis of ascorbic acid derivatives 7a–d is described. Starting from alkenylacetates 1a–d subjected to a hydrosilylation reaction, the resulting hydroxy chloro silanes 3a–d were obtained in high yield. The latter compounds were reacted with potassium phthalimide followed with hydrazine hydrate to give the amino silanols 5a–d. Ascorbic acid was then alkylated on its 3-hydroxy position to give 7a–d by means of a Mitsunobu reaction.