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Synlett 1996; 1996(1): 21-23
DOI: 10.1055/s-1996-5307
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Facile Synthesis of 1,6-Anhydrohalosugars via a Novel Rearrangement of Galactal

Roland Haeckel, Gilbert Lauer, Franz Oberdorfer*
  • *German Cancer Research Center, Department of Radiochemistry, Im Neuenheimer Feld 280, D-69120 Heidelberg, Germany, Fax: 49-6221-422572; Bitnet: radiochemie@dkfz-heidelberg.de
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Publication History

Publication Date:
31 December 2000 (online)

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A novel intramolecular vinylogous substitution of D-galactal (1) is described. The resulting 1,6-anhydro-2,3-dideoxy-β-D-threo-hex-2-enopyranose (4) can, after protection with various groups, easily be transformed into mono- and dihalocompounds (6), (9), (10), (11), (15), (16) and (17) either directly or via the Cerny epoxides (12) and (14).

1,6-Anhydrohalosugars - Cerny epoxides

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