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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ftunivmilanoair:oai:air.unimi.it:2434/182029 2024-04-21T07:46:48+00:00 Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine F. Compostella F. Ronchetti L. Franchini G. B. Giovenzana L. Panza D. Prosperi F. Compostella L. Franchini G.B. Giovenzana L. Panza D. Prosperi F. Ronchetti 2002 http://hdl.handle.net/2434/182029 http://www.scopus.com/inward/record.url?eid=2-s2.0-0037094745&partnerID=40&md5=646d94d4c75b018bf79198baf5c88bd9 https://doi.org/10.1016/S0957-4166(02)00201-X eng eng info:eu-repo/semantics/altIdentifier/wos/WOS:000176081600011 volume:13 issue:8 firstpage:867 lastpage:872 journal:TETRAHEDRON-ASYMMETRY http://www.scopus.com/inward/record.url?eid=2-s2.0-0037094745&partnerID=40&md5=646d94d4c75b018bf79198baf5c88bd9 http://hdl.handle.net/2434/182029 doi:10.1016/S0957-4166(02)00201-X info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-0037094745 Settore BIO/10 - Biochimica info:eu-repo/semantics/article 2002 ftunivmilanoair https://doi.org/10.1016/S0957-4166(02)00201-X 2024-03-27T16:31:57Z 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. Article in Journal/Newspaper Antarc* Antarctica The University of Milan: Archivio Istituzionale della Ricerca (AIR) Tetrahedron: Asymmetry 13 8 867 872 |
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Open Polar |
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The University of Milan: Archivio Istituzionale della Ricerca (AIR) |
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ftunivmilanoair |
language |
English |
topic |
Settore BIO/10 - Biochimica |
spellingShingle |
Settore BIO/10 - Biochimica F. Compostella F. Ronchetti L. Franchini G. B. Giovenzana L. Panza D. Prosperi Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine |
topic_facet |
Settore BIO/10 - Biochimica |
description |
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. |
author2 |
F. Compostella L. Franchini G.B. Giovenzana L. Panza D. Prosperi F. Ronchetti |
format |
Article in Journal/Newspaper |
author |
F. Compostella F. Ronchetti L. Franchini G. B. Giovenzana L. Panza D. Prosperi |
author_facet |
F. Compostella F. Ronchetti L. Franchini G. B. Giovenzana L. Panza D. Prosperi |
author_sort |
F. Compostella |
title |
Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine |
title_short |
Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine |
title_full |
Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine |
title_fullStr |
Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine |
title_full_unstemmed |
Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine |
title_sort |
chemoenzymatic stereoconvergent synthesis of 3-o-benzoyl azidosphingosine |
publishDate |
2002 |
url |
http://hdl.handle.net/2434/182029 http://www.scopus.com/inward/record.url?eid=2-s2.0-0037094745&partnerID=40&md5=646d94d4c75b018bf79198baf5c88bd9 https://doi.org/10.1016/S0957-4166(02)00201-X |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/wos/WOS:000176081600011 volume:13 issue:8 firstpage:867 lastpage:872 journal:TETRAHEDRON-ASYMMETRY http://www.scopus.com/inward/record.url?eid=2-s2.0-0037094745&partnerID=40&md5=646d94d4c75b018bf79198baf5c88bd9 http://hdl.handle.net/2434/182029 doi:10.1016/S0957-4166(02)00201-X info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-0037094745 |
op_doi |
https://doi.org/10.1016/S0957-4166(02)00201-X |
container_title |
Tetrahedron: Asymmetry |
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13 |
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8 |
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867 |
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872 |
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