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1-exo-Alkylidene-2,3-anhydrofuranoses: Valuable Synthons in the Preparation of Furanose-Based Templates

  作者 GOMEZ ANA M; PEDREGOSA ANA; URIEL CLARA; VALVERDE SERAFIN; CRISTOBAL LOPEZ J  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2010年-29;  页码  5619-5632  
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[摘要]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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