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• W4283271762 abstract "We report the synthesis of iminosugar C,C-glycosides starting from 6-azidoketopyranoses. Their Staudinger-azaWittig-mediated cyclization provided bicyclic N,O-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." @default.
• W4283271762 created "2022-06-23" @default.
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• W4283271762 date "2022-06-22" @default.
• W4283271762 modified "2023-10-16" @default.
• W4283271762 title "Stereoselective Access to Iminosugar <i>C</i>,<i>C</i>-Glycosides from 6-Azidoketopyranoses" @default.
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• W4283271762 doi "https://doi.org/10.1021/acs.orglett.2c01560" @default.
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