Work

Multigram-Scale Synthesis of 2,5-Dideoxy-2,5-imino- d -mannitol (DMDP) and 2,5-Dideoxy-2,5-imino- d -glucitol (DGDP) from d -Fructose and l -Sorbose Using a Regioselective Appel Reaction

Year: 2025

Type: article

Abstract: We report a practical 5 g scale stereoselective synthesis of the valuable iminosugar DMDP from d-fructose in only 7 synthetic steps and in a 70% overall yield, which doubles previously reported yields. This process requires only two chromatographic purification steps, taking advantage of a regioselective Appel reaction. The regioselective reaction has also been applied on a similar scale to prepare the C-2 diastereomer of DMDP, DGDP, from l-sorbose in 7 steps (two purifications) and 56% overall yield, albeit with diminished diastereomeric purity (d.r. 90:10). The C-5 regioselectivity has also been illustrated on d-psicose and d-tagatose, making this an attractive method for preparing pyrrolidine iminosugars or 5-thiosugars from ketopyranoses.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c02667

Authors: Peter Sunde-Brown, Gavin J. Miller, Todd A. Houston

Institutions: Griffith University, Keele University

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Griffith University, Keele University