Synthesis 1989; 1989(2): 83-88
DOI: 10.1055/s-1989-27159
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
17 September 2002 (online)

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.