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Stereoselective total synthesis of 1,4-dideoxy-1,4-imino-L-ribitol has been accomplished from D-glucose. The key step involved in this synthesis is the regioselective ring-opening of the epoxide with a tethered amido group to give the N-tosyl-3,6-dideoxy-3,6-imino-1,2- O-isopropylidene-α-D-glucofuranose.

Stereoselective Total Synthesis of 1,4-Dideoxy-1,4-imino-L-ribitol by an Intramolecular Ring Opening of Epoxide with a Tethered Amide