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Use of Protecting Groups in Carbohydrate Chemistry: An Advanced Organic Synthesis Experiment
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Abstract
A simple and inexpensive three-step reaction sequence for advanced experimental organic chemistry using D-glucosamine hydrochloride as starting material for the synthesis of 2-amino-2-deoxy-1,3,4,6-tetra-O-acetyl -b-D-glucopyranose hydrochloride is described. The aim of the experiment is to protect the hydroxyl groups of D-glucosamine leaving its amino group as hydrochloride salt. The experiment deals only with protection and deprotection reactions.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
CarbohydratesCiting Articles
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
Stereochemical Control in Carbohydrate Chemistry
Emma M. Dangerfield and Bridget L. Stocker , Rhys Batchelor , Peter T. Northcote and Joanne E. HarveyJournal of Chemical Education2008 85 (5), 689Stereochemical Control in Carbohydrate Chemistry
Emma M. Dangerfield and Bridget L. Stocker , Rhys Batchelor , Peter T. Northcote and Joanne E. HarveyJournal of Chemical Education2008 85 (5), 689Carbohydrates, in the form of glycoconjugates, have recently been shown to control a wide range of cellular processes. Accordingly, students interested in the study of organic chemistry and biomedical sciences should be exposed to carbohydrate chemistry. ...
Synthesis and Use of Mechanism-Based Protein-Profiling Probes for Retaining β-d-Glucosaminidases Facilitate Identification of Pseudomonas aeruginosa NagZ
Keith A. Stubbs, Adrian Scaffidi, Aleksandra W. Debowski, Brian L. Mark, Robert V. Stick, and David J. VocadloJournal of the American Chemical Society2008 130 (1), 327-335Synthesis and Use of Mechanism-Based Protein-Profiling Probes for Retaining β-d-Glucosaminidases Facilitate Identification of Pseudomonas aeruginosa NagZ
Keith A. Stubbs, Adrian Scaffidi, Aleksandra W. Debowski, Brian L. Mark, Robert V. Stick, and David J. VocadloJournal of the American Chemical Society2008 130 (1), 327-335The NagZ class of retaining exo-glucosaminidases play a critical role in peptidoglycan recycling in Gram-negative bacteria and the induction of resistance to -lactams. Here we describe the concise synthesis of 2-azidoacetyl-2-deoxy-5-fluoro--d-...
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 MeoJournal of Chemical Education2006 83 (5), 782Acetal Protecting Groups in the Organic Laboratory: Synthesis of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside
Alexei V. Demchenko , Papapida Pornsuriyasak and Cristina De MeoJournal of Chemical Education2006 83 (5), 782A 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 ...
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- Received: August 03, 2009
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