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

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 hyd...

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Bibliographic Details
Published in:Tetrahedron 2002-11, Vol.58 (45), p.9249-9256
Main Authors: Vilaça, Gil, Rubio, Cyril, Susperregui, Jacques, Latxague, Laurent, Déléris, Gérard
Format: Article
Language:English
Subjects:
ascorbic acid derivatives
bone
Mitsunobu reaction
silicon
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Summary: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. Four l-ascorbic acid derivatives have been synthesized via a Mitsunobu reaction and the proposed structure was confirmed by 2D NMR spectroscopy.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)01185-7