Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

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 thes...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: Compostella, F, Franchini, F, Giovenzana, G. B, Panza, L, PROSPERI, DAVIDE, Ronchetti, F.
Other Authors: Giovenzana, G, Prosperi, D, Ronchetti, F
Format: Article in Journal/Newspaper
Language:English
Published: Pergamon 2002
Subjects:
sintesi organica
reazioni enzimatiche
BIO/10 - BIOCHIMICA
Antarc*
Antarctica
Online Access:http://hdl.handle.net/10281/24682
https://doi.org/10.1016/S0957-4166(02)00201-X
Description
Summary: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

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