Stereoselective synthesis of (2S,3S,4R,5S)-3,4-dihydroxy-2,5-dihydroxymethyl pyrrolidine from l-sorbose

• We have developed a new method to produce DMDP.
• This method can give access to several analogues for structures/activities relationships.
• A stereoselective reduction has been observed and rationalised.

One of the most frequently synthesized iminosugar derivatives is DMDP. Starting from l-sorbose, a practical method for the synthesis of derivatives of this five-membered iminocyclitol has been developed, involving straightforward steps and a convenient selective reduction of a ketoxime intermediate.

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