RT Journal Article
T1 Stable Ditriflates of D-Glucose in the Synthesis of Iminosugars and Polyhydroxylated Pipecolic Acids
A1 Balo, Rosalino
A1 Fernández, Andrés
A1 Reza Ramos, David
A1 López Carracedo, Pablo
A1 Fleet, George W. J.
A1 Estévez Cabanas, Ramón José
A1 Estévez Cabanas, Juan Carlos
K1 Iminosugars
K1 Pipecolid acids
K1 Sugar diols
K1 Stereoselective synthesis
AB 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.
PB Wiley
YR 2024
FD 2024-10-21
LK https://hdl.handle.net/10347/38158
UL https://hdl.handle.net/10347/38158
LA eng
NO Balo, 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
NO Supporting information for this article is available on the WWW under https://doi.org/10.1002/ejoc.202400395
NO Agencia Estatal de Investigación: CPP2021-009090, PID2022-136848NB−I00
NO Xunta de Galicia: ED431C 2022/21, ED431F 2020/05
NO Centro singular de investigación de Galicia accreditation: ED431G 2019/03
NO Ministerio de Educación, Cultura y Deporte: FPU13/01243
NO Xunta de Galicia: ED481A-2019/141
DS Minerva
RD 26 abr 2026