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Synlett 2000; 2000(6): 0817-0819
DOI: 10.1055/s-2000-6694
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Stereoselective Synthesis of an Aminocyclopentitol Analog of α-l-Fucose via an Allylic Bromohydrin

Adrian Blaser* , Jean-Louis Reymond
  • *Department of Chemistry & Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland; Fax +41 31 631 80 57; E-mail: jean-louis.reymond@ioc.unibe.ch
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Publikationsdatum:
31. Dezember 2000 (online)

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Selective opening of allylic epoxide 4 with lithium bromide in acetic acid provides an allylic bromohydrin (5). Chemo- and stereoselective hydrogenation of the corresponding benzyl carbamate 6 and intramolecular cyclization gives, after deprotection, (1R,2R,3R,4R,5R) 4-amino-5-methyl-cyclopentane-1,2,3-triol 3, an analog of α-l-fucose. This synthetic sequence provides one of the few stereoselective approaches to alpha-configurated aminocyclopentitols.

aminations - amino alcohols - carbohydrates - glycosidases - stereoselective synthesis