The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of these diastereoisomers, mediated by lipase from Candida antarctica, Mitsunobu inversion on the wrong diastereoisomer and extremely efficient introduction of azide using a chloromesylate leaving group affords the title compound in 30% overall yield.

Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine / F. Compostella, L. Franchini, G.B. Giovenzana, L. Panza, D. Prosperi, F. Ronchetti. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 13:8(2002), pp. 867-872. [10.1016/S0957-4166(02)00201-X]

Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

F. Compostella
Primo
;
F. Ronchetti
Ultimo
2002

Abstract

The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of these diastereoisomers, mediated by lipase from Candida antarctica, Mitsunobu inversion on the wrong diastereoisomer and extremely efficient introduction of azide using a chloromesylate leaving group affords the title compound in 30% overall yield.
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/182029
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