Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

Federica Compostella; Laura Franchini; Giovanni Battista Giovenzana; Luigi Panza; Davide Prosperi; Fiamma Ronchetti

doi:10.1016/S0957-4166(02)00201-X

Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

Federica Compostella
, Laura Franchini
, Giovanni Battista Giovenzana
, Luigi Panza
, Davide Prosperi
, Fiamma Ronchetti

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	867-872
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	13
Issue number	8
DOIs	https://doi.org/10.1016/S0957-4166(02)00201-X
Publication status	Published - 15 May 2002

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title = "Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine",

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.",

author = "Federica Compostella and Laura Franchini and Giovenzana, \{Giovanni Battista\} and Luigi Panza and Davide Prosperi and Fiamma Ronchetti",

note = "Funding Information: The authors thank the MIUR, the University of Piemonte Orientale and the University of Milano for financial support.",

year = "2002",

month = may,

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doi = "10.1016/S0957-4166(02)00201-X",

language = "English",

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journal = "Tetrahedron Asymmetry",

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TY - JOUR

T1 - Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

AU - Compostella, Federica

AU - Franchini, Laura

AU - Giovenzana, Giovanni Battista

AU - Panza, Luigi

AU - Prosperi, Davide

AU - Ronchetti, Fiamma

N1 - Funding Information: The authors thank the MIUR, the University of Piemonte Orientale and the University of Milano for financial support.

PY - 2002/5/15

Y1 - 2002/5/15

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0037094745

U2 - 10.1016/S0957-4166(02)00201-X

DO - 10.1016/S0957-4166(02)00201-X

M3 - Article

SN - 0957-4166

VL - 13

SP - 867

EP - 872

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 8

ER -

Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

Abstract

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