1257399-09-9Relevant academic research and scientific papers
1-exo-alkylidene-2,3-anhydrofuranoses: Valuable synthons in the preparation of furanose-based templates
Gomez, Ana M.,Pedregosa, Ana,Uriel, Clara,Valverde, Serafin,Lopez, J. Cristobal
experimental part, p. 5619 - 5632 (2010/12/25)
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. 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.
