We report the synthesis of iminosugar ,-glycosides starting from 6-azidoketopyranoses. Their Staudinger-azaWittig-mediated cyclization provided bicyclic ,-acetals, which were stereoselectively opened with AllMgBr to afford β-hydroxyazepanes with a quaternary carbon α to the nitrogen. Their ring contraction via a β-aminoalcohol rearrangement produced the six-membered l-iminosugars with two functional handles at the pseudoanomeric position. Inversion of the free OH at the azepane level furnished the d-iminosugars.
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