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Access to Pyrrolidine Imino Sugars via Tin(II)-Mediated Aldol Reactions of Bislactim Ethers: Synthesis of 2,5-Dideoxy-2,5-Imino-D-Glucitol
| dc.contributor.author | Blanco, Olga | |
| dc.contributor.author | Pato Pérez, Cristina María | |
| dc.contributor.author | Ruiz, María | |
| dc.contributor.author | Ojea, Vicente | |
| dc.date.accessioned | 2024-08-09T07:49:02Z | |
| dc.date.available | 2024-08-09T07:49:02Z | |
| dc.date.issued | 2008-09-05 | |
| dc.identifier.citation | O. Blanco, C. Pato, M. Ruiz and V. Ojea, Access to pyrrolidine imino sugarsvia tin(II)-mediated aldol reactions of bislactim ethers: synthesis of 2,5-dideoxy-2,5-imino-D-glucitol, Org. Biomol. Chem., 2008, 6, 3967–3969. | es_ES |
| dc.identifier.issn | 1477-0539 | |
| dc.identifier.uri | http://hdl.handle.net/2183/38499 | |
| dc.description | Author accepted manuscript | es_ES |
| dc.description.abstract | [Abstract] 2,5-Dideoxy-2,5-imino-D-glucitol (DGDP) has been synthesized via the tin(II)-mediated anti-selective aldol reaction of bislactim ether 5 and a 3-O-silylated 2,4-ethylidene-D-erythrose derivative 6. In accordance with density functional theory calculations (at the B3LYP/cc-pVDZ-PP level), pericyclic transition structures with a boat-like conformation and a stabilizing hydrogen bond can account for the unexpected stereoselectivity. | es_ES |
| dc.description.sponsorship | We gratefully acknowledge Ministerio de Ciencia y Tecnología (BQU2003-00692) and Xunta de Galicia (PGIDIT05BTF10301PR) for financial support. The authors are indebted to Centro de Supercomputación de Galicia for providing computer facilities. O. B. thanks Xunta de Galicia for an “Isidro Parga Pondal” position at Universidade da Coruña | es_ES |
| dc.description.sponsorship | Xunta de Galicia; PGIDIT05BTF10301PR | es_ES |
| dc.language.iso | eng | es_ES |
| dc.publisher | Royal Society of Chemistry | es_ES |
| dc.relation | info:eu-repo/grantAgreement/MICYT/Plan Nacional de I+D+i 2000-2003/BQU2003-00692/ES/ | es_ES |
| dc.relation.uri | https://doi.org/10.1039/B810878A | es_ES |
| dc.title | Access to Pyrrolidine Imino Sugars via Tin(II)-Mediated Aldol Reactions of Bislactim Ethers: Synthesis of 2,5-Dideoxy-2,5-Imino-D-Glucitol | es_ES |
| dc.type | info:eu-repo/semantics/article | es_ES |
| dc.rights.access | info:eu-repo/semantics/openAccess | es_ES |
| UDC.journalTitle | Organic & Biomolecular Chemistry | es_ES |
| UDC.volume | 6 | es_ES |
| UDC.issue | 21 | es_ES |
| UDC.startPage | 3967 | es_ES |
| UDC.endPage | 3969 | es_ES |
| dc.identifier.doi | 10.1039/B810878A |
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