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Synthesis 1989; 1989(2): 83-88
DOI: 10.1055/s-1989-27159
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Enantiomerically Pure 2-(Carbamoyloxy)oxiranes and Their Utility in the Synthesis of D- and L-3,6-Dideoxy-3-C-methylhexofuranosides via the Homoaldol Reaction

Dieter Hoppe* , Gerhard Tarara, Marcus Wilckens
  • *Institut für Organische Chemie der Universität Kiel, Olshausenstr, 40-60, D-2300 Kiel 1, Federal Republic of Germany
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Publication Date:
17 September 2002 (online)

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As an example of a novel flexible strategy in the rapid enantioselective construction of branched carbohydrate analogues by the homoaldol reaction, the title compounds were synthesized. α-Metalated (E)-2-butenyl N,N-diisopropylcarbamate is added to (S)- or (R)-2-benzyloxypropanal. The homoaldol adducts are epoxidized; methanolysis affords furanosides of branched 3,6-dideoxyaldohexoses, or, hydrolysis yields the furanoses.