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1-exo-alkylidene-2,3-anhydrofuranoses: Valuable synthons in the preparation of furanose-based templates

AuthorsGómez, Ana M. ; Pedregosa, A.; Uriel, Clara ; Valverde, Serafín; López, J. Cristobal
Issue Date2010
PublisherJohn Wiley & Sons
CitationEuropean Journal of Organic Chemistry: 5619- 5632 (2010)
AbstractHighly 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. A highly functionalized 1-exo-alkylidene-2,3-anhydro-furanose, available in four steps from D-mannose, is a useful substrate that can be transformed into a variety of furanose derivatives including compounds with up to four sites for diversity. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Identifiersdoi: 10.1002/ejoc.201000612
issn: 1434-193X
e-issn: 1099-0690
Appears in Collections:(IQOG) Artículos
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