One-pot Orthogonal Protection of Carbohydrates: An Advanced Organic Chemistry Laboratory Experiment

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 20 (2015) pp 151-153

One-pot Orthogonal Protection of Carbohydrates: An Advanced Organic Chemistry Laboratory Experiment

Robert L. Woodward*^,†, Amanda L. Dragan^†, Alyssa M. Greenwell^‡, Emily A. Loosli^§ and Christopher J. Holmes^†

^†Department of Chemistry & Biochemistry, The University of Mount Union, 1972 Clark Avenue, Alliance, OH 44601, woodwarl@mountunion.edu; ^‡The Ohio State University College of Medicine, 453 West 10th Avenue, Columbus, OH 43210; ^§Ohio University Heritage College of Osteopathic Medicine, 204 Grosvenor Hall, Athens, OH 45701,
Received May 7, 2015. Accepted June 4, 2015.

Published: 23 June 2015

Abstract. A one-pot orthogonal protection strategy for N-acetyl-D-glucsoamine was developed as an advanced organic chemistry laboratory experiment. This experiment can be completed in three laboratory periods and exposes students to fundamental synthetic techniques including performing reactions under oxygen/moisture-free conditions, TLC, acid-base extraction, flash column chromatography, and NMR spectroscopy. Furthermore, this experiment can readily be adapted to evaluate the benefits of the one-pot reaction as well as the potential for use of various other carbohydrates.

Key Words: Laboratories and Demonstrations; organic chemistry; carbohydrates; one-pot reaction; protecting groups

(*) Corresponding author. (E-mail: woodwarl@mountunion.edu )

Article in PDF format (77 KB) HTML format

Supporting Materials:

Additional experimental procedures, results from reactions using other carbohydrates, CAS numbers, and mass spectrometry & NMR data (113 KB).