Balo, RosalinoFernández, AndrésReza Ramos, DavidLópez Carracedo, PabloFleet, George W. J.Estévez Cabanas, Ramón JoséEstévez Cabanas, Juan Carlos2024-12-132024-12-132024-10-21Balo, 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.202400395https://hdl.handle.net/10347/38158Supporting information for this article is available on the WWW under https://doi.org/10.1002/ejoc.202400395A 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.engAttribution-NonCommercial-NoDerivatives 4.0 International. © 2024 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbHhttp://creativecommons.org/licenses/by-nc-nd/4.0/IminosugarsPipecolid acidsSugar diolsStereoselective synthesis2306 Química orgánicajournal article10.1002/ejoc.2024003951099-0690open access