Stable ditriflates of D-glucose in the synthesis of iminosugars and polyhydroxyolated pipecolic acids

26 December 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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 iminoacid 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.

Keywords

Carbohydrates
iminosugars
glycosidase inhibitors
pipecolic acids
stereoselective synthesis.

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