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Synthesis 1990; 1990(4): 285-291
DOI: 10.1055/s-1990-26854
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Oxirane Ring Opening of Anhydrosugars with Alkynyl- and Alkenylaluminates

Tord Inghardt* , Torbjörn Frejd
  • *Organic Chemistry 2 Chemical Center The Lund Institute of Technology, P.O. Box 124, S-221 00 Lund, Sweden
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Publication Date:
17 September 2002 (online)

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The oxirane ring opening of 2,3-anhydro-pentopyranosides and 2,3-anhydro-hexopyranosides with organoaluminate reagents is described. By the use of trialkylalkynylaluminates, deoxy-alkynyl sugars are obtained in good yields. Trialkylalkenylaluminates are less efficient and react only with the pentosides. Vinylmagnesium bromide is used as an alternative reagent for the introduction of a vinyl group.

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