Synthesis of a Partially Protected Azidodeoxy Sugar. A Project Suitable for the Advanced Undergraduate Organic Chemistry Laboratory

• Peter Norris ^[1] ; Scott Freeze ^[1] ; Christopher J. Gabriel ^[1]
  1. [1] Youngstown State University

     Youngstown State University

     City of Youngstown, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 78, Nº 1, 2001, pág. 75
• Idioma: inglés
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• Resumen

  • The synthetic chemistry of carbohydrates provides a wealth of possible experiments for the undergraduate organic chemistry laboratory. However, few appropriate examples have been developed to date. With this simple two-step synthesis of a partially protected azidodeoxy sugar, we demonstrate several important concepts introduced in undergraduate chemistry (alcohol activation, steric hindrance, nucleophilic substitution) while offering products that are readily amenable to analysis by high field NMR. Students are exposed to techniques such as monitoring reactions by TLC, workup of reaction mixtures, and isolation by flash chromatography. Suitable methods for analysis of products include NMR, IR, MS, and polarimetry.