Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 29, Pages 5619-5632Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000612
Keywords
Carbohydrates; Glycals; Molecular diversity; Template synthesis; Epoxidation
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Funding
- Ministerio de Ciencia e Innovacion (MICINN) [CTQ2006-15279-C03-02, CTQ2009-10343]
- Comunidad de Madrid [S2009/PPQ-1752]
- Janssen-Cilag SA
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Highly functionalized 1-exo-alkylidene-2,3-anhydro-, and 1'-halo-1-exo-alkylidene-2,3-anhydrofuranoses can be prepared in four or five steps, respectively, from D-mannose. These compounds feature a variety of functionalities, including a double bond, an oxirane, an allylic oxirane and (in the case of the 1'-halo derivative) an alkenyl halide. The reactivity of each functionality in these derivatives has been explored, and the usefulness of these substrates has been demonstrated with the preparation of furanose-based carbohydrate templates with up to four sites of molecular diversity.
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