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http://hdl.handle.net/2445/119330
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DC Field | Value | Language |
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dc.contributor.author | Fuente Cebrián, Àlex de la | - |
dc.contributor.author | Verdaguer i Espaulella, Xavier | - |
dc.contributor.author | Riera i Escalé, Antoni | - |
dc.date.accessioned | 2018-01-26T10:37:53Z | - |
dc.date.available | 2018-12-21T06:10:16Z | - |
dc.date.issued | 2017-12-21 | - |
dc.identifier.issn | 1434-193X | - |
dc.identifier.uri | http://hdl.handle.net/2445/119330 | - |
dc.description.abstract | A stereoselective synthesis of 2-acetamido-1,2-dideoxyaltronojirimycin (8) and its manno epimer 9 is described. The synthetic approach is based on key bicyclic carbamate 7, which is easily accessible with high enantiomeric purity on a multigram scale by Sharpless asym. epoxidn. of 1,4-pentadien-3-ol or 2,4-pentadien-1-ol. This procedure completes an efficient stereodivergent approach to five isomers of 2-acetamido-1,2-dideoxyiminosugars in high overall yields starting from the same key intermediate 7. The approach described in this paper is based on control of the stereoselectivity of the sulfite ring-opening reaction to give retention of configuration through anchimeric assistance from the endocyclic amine. | - |
dc.format.extent | 7 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Wiley-VCH | - |
dc.relation.isformatof | Versió postprint del document publicat a: https://doi.org/10.1002/ejoc.201701282 | - |
dc.relation.ispartof | European Journal of Organic Chemistry, 2017, vol. 2017, num. 47, p. 7179-7185 | - |
dc.relation.uri | https://doi.org/10.1002/ejoc.201701282 | - |
dc.rights | (c) Wiley-VCH, 2017 | - |
dc.source | Articles publicats en revistes (Química Inorgànica i Orgànica) | - |
dc.subject.classification | Disseny de medicaments | - |
dc.subject.classification | Inhibidors enzimàtics | - |
dc.subject.other | Drug design | - |
dc.subject.other | Enzyme inhibitors | - |
dc.title | Stereodivergent syntheses of altro and manno stereoisomers of 2-acetamido-1,2-dideoxynojirimycin | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 675635 | - |
dc.date.updated | 2018-01-26T10:37:53Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
Files in This Item:
File | Description | Size | Format | |
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675635.pdf | 566.7 kB | Adobe PDF | View/Open |
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