Stable Ditriflates of D-Glucose in the Synthesis of Iminosugars and Polyhydroxylated Pipecolic Acids

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dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánica
dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)
dc.contributor.authorBalo, Rosalino
dc.contributor.authorFernández, Andrés
dc.contributor.authorReza Ramos, David
dc.contributor.authorLópez Carracedo, Pablo
dc.contributor.authorFleet, George W. J.
dc.contributor.authorEstévez Cabanas, Ramón José
dc.contributor.authorEstévez Cabanas, Juan Carlos
dc.date.accessioned2024-12-13T10:31:16Z
dc.date.available2024-12-13T10:31:16Z
dc.date.issued2024-10-21
dc.descriptionSupporting information for this article is available on the WWW under https://doi.org/10.1002/ejoc.202400395
dc.description.abstractA synthesis of the five membered iminosugar DAB and a divergent synthesis of the six membered iminosugar 1-dehydromannojirimycin (DMJ) and the corresponding sugar imino acid are reported. They involve double nucleophilic displacements of a D-xylose ditriflate by benzyl carbazate and a D-glucose ditriflate by allyl amine, respectively. They are followed by a similar protocol consisting of hydrolysis and oxidation or reduction of the resulting bicyclic glycosides. This allowed DMJ to be obtained from the cheap sugar D-glucose.
dc.description.peerreviewedSI
dc.description.sponsorshipAgencia Estatal de Investigación: CPP2021-009090, PID2022-136848NB−I00
dc.description.sponsorshipXunta de Galicia: ED431C 2022/21, ED431F 2020/05
dc.description.sponsorshipCentro singular de investigación de Galicia accreditation: ED431G 2019/03
dc.description.sponsorshipMinisterio de Educación, Cultura y Deporte: FPU13/01243
dc.description.sponsorshipXunta de Galicia: ED481A-2019/141
dc.identifier.citationBalo, R., Fernández, A., Reza, D., López, P., Fleet, G. W. J., Estévez, R. J., & Estévez, J. C. (2024). Stable Ditriflates of D-Glucose in the Synthesis of Iminosugars and Polyhydroxylated Pipecolic Acids. "EurJOC (European Journal of Organic Chemistry)", 27(42). https://doi.org/10.1002/ejoc.202400395
dc.identifier.doi10.1002/ejoc.202400395
dc.identifier.essn1099-0690
dc.identifier.urihttps://hdl.handle.net/10347/38158
dc.issue.number42
dc.journal.titleEurJOC (European Journal of Organic Chemistry)
dc.language.isoeng
dc.publisherWiley
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/CPP2021-009090/ES/CAPN12-IO: DESARROLLO PRECLÍNICO Y PRIMER ENSAYO CLÍNICO EN HUMANOS DE UN INHIBIDOR SELECTIVO PARA CALPAÍNA-12 COMO UNA NUEVA ESTRATEGIA PARA LA INMUNOTERAPIA DEL CÁNCER./
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-136848NB−I00/ES/POLIMEROS HELICOIDALES COVALENTES Y SUPRAMOLECULARES: DISEÑO, ESTRUCTURA Y PROPIEDADES ESTIMULO RESPUESTA/
dc.relation.publisherversionhttps://doi.org/10.1002/ejoc.202400395
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 International. © 2024 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH
dc.rights.accessRightsopen access
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectIminosugars
dc.subjectPipecolid acids
dc.subjectSugar diols
dc.subjectStereoselective synthesis
dc.subject.classification2306 Química orgánica
dc.titleStable Ditriflates of D-Glucose in the Synthesis of Iminosugars and Polyhydroxylated Pipecolic Acids
dc.typejournal article
dc.type.hasVersionVoR
dc.volume.number27
dspace.entity.typePublication
relation.isAuthorOfPublication19cdf079-dc1b-48b2-8bc9-c73d3601f141
relation.isAuthorOfPublication86b5b898-6642-4dd7-b2ee-117e2f4838ff
relation.isAuthorOfPublication.latestForDiscovery86b5b898-6642-4dd7-b2ee-117e2f4838ff

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