Prev. Article Next Article Table of Contents

Article

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

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Peter Norris , Scott Freeze and Christopher J. Gabriel

Department of Chemistry, Youngstown State University, Youngstown, OH 44555-3663

J. Chem. Educ., 2001, 78 (1), p 75

DOI: 10.1021/ed078p75

Publication Date (Web): January 1, 2001

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Carbohydrates

View: Hi-Res PDF | PDF w/ Links

Citing Articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 3 ACS Journal articles (3 most recent appear below).

Acetal Protecting Groups in the Organic Laboratory: Synthesis of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside
Alexei V. Demchenko , Papapida Pornsuriyasak and Cristina De Meo
Journal of Chemical Education2006 83 (5), 782
- Acetal Protecting Groups in the Organic Laboratory: Synthesis of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside
  Alexei V. Demchenko , Papapida Pornsuriyasak and Cristina De Meo
  Journal of Chemical Education2006 83 (5), 782
  A laboratory procedure for the synthesis of methyl 4,6-O-benzylidene-α-D-glucopyranoside is described. This compound is obtained in one synthetic step from commercially available methyl α-D-glucopyranoside. Purification of the target compound is achieved ...
  Abstract | Hi-Res PDF | PDF w/ Links
Use of 1H NMR in Assigning Carbohydrate Configuration in the Organic Laboratory
John L. Sorensen , Ross Witherell and Lois M. Browne
Journal of Chemical Education2006 83 (5), 785
- Use of 1H NMR in Assigning Carbohydrate Configuration in the Organic Laboratory
  John L. Sorensen , Ross Witherell and Lois M. Browne
  Journal of Chemical Education2006 83 (5), 785
  This article describes a laboratory experiment suitable for an advanced undergraduate organic laboratory class that combines synthetic organic chemistry and 1H NMR in the determination of the identity of a simple carbohydrate. The focus of the laboratory ...
  Abstract | Hi-Res PDF | PDF w/ Links
Carbohydrate Analysis: Can We Control the Ripening of Bananas?
S. Todd Deal , Catherine E. Farmer and Paul F. Cerpovicz
Journal of Chemical Education2002 79 (4), 479
- Carbohydrate Analysis: Can We Control the Ripening of Bananas?
  S. Todd Deal , Catherine E. Farmer and Paul F. Cerpovicz
  Journal of Chemical Education2002 79 (4), 479
  We have developed an experiment for nutritional/introductory biochemistry courses that focuses on carbohydrate analysis--specifically, the carbohydrates found in bananas and the change in carbohydrate composition as the banana ripens. Pairs of students ...
  Abstract | Hi-Res PDF | PDF w/ Links