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...
| Published in: | Tetrahedron: Asymmetry |
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| Main Authors: | , , , , , |
| Other Authors: | , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Pergamon
2002
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| Subjects: | |
| Online Access: | http://hdl.handle.net/10281/24682 https://doi.org/10.1016/S0957-4166(02)00201-X |
| _version_ | 1833106848068141056 |
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| author | Compostella, F Franchini, F Giovenzana, G. B Panza, L PROSPERI, DAVIDE Ronchetti, F. |
| author2 | Compostella, F Franchini, F Giovenzana, G Panza, L Prosperi, D Ronchetti, F |
| author_facet | Compostella, F Franchini, F Giovenzana, G. B Panza, L PROSPERI, DAVIDE Ronchetti, F. |
| author_sort | Compostella, F |
| collection | Università degli Studi di Milano-Bicocca: BOA (Bicocca Open Archive) |
| container_issue | 8 |
| container_start_page | 867 |
| container_title | Tetrahedron: Asymmetry |
| container_volume | 13 |
| 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 |
| format | Article in Journal/Newspaper |
| genre | Antarc* Antarctica |
| genre_facet | Antarc* Antarctica |
| id | ftunivmilanobic:oai:boa.unimib.it:10281/24682 |
| institution | Open Polar |
| language | English |
| op_collection_id | ftunivmilanobic |
| op_container_end_page | 872 |
| op_doi | https://doi.org/10.1016/S0957-4166(02)00201-X |
| op_relation | info:eu-repo/semantics/altIdentifier/wos/WOS:000176081600011 volume:13 issue:8 firstpage:867 lastpage:872 journal:TETRAHEDRON-ASYMMETRY http://hdl.handle.net/10281/24682 |
| publishDate | 2002 |
| publisher | Pergamon |
| record_format | openpolar |
| spelling | ftunivmilanobic:oai:boa.unimib.it:10281/24682 2025-05-25T13:45:03+00:00 Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine Compostella, F Franchini, F Giovenzana, G. B Panza, L PROSPERI, DAVIDE Ronchetti, F. Compostella, F Franchini, F Giovenzana, G Panza, L Prosperi, D Ronchetti, F 2002 http://hdl.handle.net/10281/24682 https://doi.org/10.1016/S0957-4166(02)00201-X eng eng Pergamon info:eu-repo/semantics/altIdentifier/wos/WOS:000176081600011 volume:13 issue:8 firstpage:867 lastpage:872 journal:TETRAHEDRON-ASYMMETRY http://hdl.handle.net/10281/24682 sintesi organica reazioni enzimatiche Settore BIOS-07/A - Biochimica info:eu-repo/semantics/article 2002 ftunivmilanobic https://doi.org/10.1016/S0957-4166(02)00201-X 2025-04-28T01:57:20Z 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 Università degli Studi di Milano-Bicocca: BOA (Bicocca Open Archive) Tetrahedron: Asymmetry 13 8 867 872 |
| spellingShingle | sintesi organica reazioni enzimatiche Settore BIOS-07/A - Biochimica Compostella, F Franchini, F Giovenzana, G. B Panza, L PROSPERI, DAVIDE Ronchetti, F. Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine |
| title | 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_short | Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine |
| title_sort | chemoenzymatic stereoconvergent synthesis of 3-o-benzoyl azidosphingosine |
| topic | sintesi organica reazioni enzimatiche Settore BIOS-07/A - Biochimica |
| topic_facet | sintesi organica reazioni enzimatiche Settore BIOS-07/A - Biochimica |
| url | http://hdl.handle.net/10281/24682 https://doi.org/10.1016/S0957-4166(02)00201-X |