Stable Ditriflates of D‐Glucose in the Synthesis of Iminosugars and Polyhydroxylated Pipecolic Acids
Abstract A 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.
Authors
- Rosalino Balo (ORCID: https://orcid.org/0000-0001-9881-0826)
- Plazarte López (ORCID: https://orcid.org/0000-0002-8632-7877)
- George W. J. Fleet (ORCID: https://orcid.org/0000-0003-1903-270X)
- Juan C. Estévez (ORCID: https://orcid.org/0000-0001-9468-9045)
- Ramón J. Estévez (ORCID: https://orcid.org/0000-0002-3764-0832)
- David Reza (ORCID: https://orcid.org/0000-0002-6075-0079)
- Andrés Fernández (ORCID: https://orcid.org/0009-0001-7385-3106)
Institutions
- Universidade de Santiago de Compostela (ES)
- University of Oxford (GB)
- Center for Research in Molecular Medicine and Chronic Diseases (ES)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2024-10-21
- DOI
- https://doi.org/10.1002/ejoc.202400395
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- European Commission
- Ministerio de Educación, Cultura y Deporte
- Xunta de Galicia
- Centro Singular de Investigación de Galicia
- European Regional Development Fund
- Agencia Estatal de Investigación