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

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

Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

PROSPERI, DAVIDE;
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
Articolo in rivista - Articolo scientifico
sintesi organica; reazioni enzimatiche
English
2002
13
8
867
872
none
Compostella, F., Franchini, F., Giovenzana, G., Panza, L., Prosperi, D., Ronchetti, F. (2002). Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine. TETRAHEDRON-ASYMMETRY, 13(8), 867-872 [10.1016/S0957-4166(02)00201-X].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/24682
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