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Synlett 2001; 2001(8): 1332-1334
DOI: 10.1055/s-2001-16049
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Imino Glycals in Synthesis: Preparation of Novel Deoxymannojirimycin Analogues

Jérôme Désiré* , Michael Shipman
  • *School of Chemistry, University of Exeter, Stocker Road, Exeter, EX4 4QD, UK; Fax + 44 1392 26 34 34; E-mail: m.shipman@exeter.ac.uk
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Publication Date:
31 December 2001 (online)

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The synthesis of imino glucal 2 from tetra-O-benzyl-d-glucopyranose in 7 steps is described. This imino sugar building block is converted into conformationally constrained deoxymannojirimycin analogue (+)-9 by means of a stereocontrolled cyclopropanation followed by a two step deprotection sequence. Regioselective fission of the cyclopropane ring prior to deprotection provides access to related analogue (+)-11.

carbohydrates - piperidines - stereoselective synthesis - imino glycals - glycosidases

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