Oxirane Ring Opening of Anhydrosugars with Alkynyl- and Alkenylaluminates
- 1 January 1990
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1990 (04) , 285-291
- https://doi.org/10.1055/s-1990-26854
Abstract
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.Keywords
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