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In the Laboratory
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Synthesis of Methyl 2,3,5-Tri-O-benzoyl-a-D-arabinofuranoside in the Organic Laboratory
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Christopher S. Callam and Todd L. Lowary
Department of Chemistry, The Ohio State University, Columbus, OH 43210
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January 2001
Vol. 78 No. 1
p. 73
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| Abstract |
We report an organic chemistry laboratory experiment in which methyl 2,3,5-tri-O-benzoyl-a-D-arabinofuranoside is synthesized. The product is obtained in two steps from commercially available D-arabinose, via Fischer glycosylation and benzoylation. The product is easily purified by crystallization. The primary purpose in implementing this experiment was to give students additional exposure to carbohydrate chemistry. In addition, the experiment provides an opportunity to discuss a number of other topics including kinetic vs thermodynamic control of reactions, mutarotation, the synthesis of esters, recrystallization, the separation of diastereomers, and optical activity. It is also possible to incorporate 2-D NMR spectroscopy into this experiment.
See Correction to this article.
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| Supplement |
Notes for the student, detailed notes for the instructor, and sample spectra are available.
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| More Information |
Citation |
Callam, Christopher S.; Lowary, Todd L. J. Chem. Educ. 2001 78 73.
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Keywords |
Carbohydrates; Medicinal Chemistry; NMR Spectrometry; Organic Synthesis; Laboratory Instruction
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History |
Created:
Last Updated: |
November 30, 2000
August 31, 2005
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Link to Correction added (May 2004).
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| Home > JCE Print > Journal of Chemical Education > Issues >
2001
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January
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