Stable Ditriflates of D‐Glucose in the Synthesis of Iminosugars and Polyhydroxylated Pipecolic Acids
Year: 2024
Type: article
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, Andrés Fernández, David Reza, Pablo López, George W. J. Fleet, Ramón J. Estévez, Juan C. Estévez
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,330
OpenAlex ID: W4403658019