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  Home > JCE Print > Journal of Chemical Education > Issues > 2001  > January  >
In the Laboratory
Synthesis of a Partially Protected Azidodeoxy Sugar. A Project Suitable for the Advanced Undergraduate Organic Chemistry Laboratory
Peter Norris, Scott Freeze, and Christopher J. Gabriel
Department of Chemistry, Youngstown State University, Youngstown, OH 44555-3663
Cover
January 2001
Vol. 78 No. 1
p. 75
Abstract
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.
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*  Citation
 Norris, Peter; Freeze, Scott; Gabriel, Christopher J. J. Chem. Educ. 2001 78 75.
*  Keywords
 Carbohydrates; Chromatography; NMR Spectrometry; Organic Synthesis; Organic Chemistry; Laboratory Instruction
*  History
 Created:
Last Updated:		 November 30, 2000
August 31, 2005
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