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Protecting Groups in Carbohydrate Chemistry
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Abstract
The most important protecting groups in carbohydrate chemistry are reviewed. The paper is aimed at those beginning to specialize in synthetic carbohydrate chemistry and at teachers with other specialties who wish to go beyond the content of general organic chemistry textbooks. Acetals and ketals are of fundamental importance in carbohydrate chemistry and their chemistry is presented first. In contrast to the base stability of the acetals, are the base labile esters. The complimentary use of these two protecting methods is illustrated. Methyl and benzyl ethers have a long history both in synthetic carbohydrate chemistry and in the structural studies of polysaccharides. In synthetic work benzyl ethers are the most useful. Silyl ethers are also well established in carbohydrate chemistry and the use of these protecting methods is illustrated. Phase transfer reactions and the use of cyclic stannylene derivatives to enhance the regioselectivity in the introduction of protecting groups, especially ethers, is discussed as well as some results optained with stannous chloride catalyzed reactions of diaryldiphenylmethanes with vicinal diols which gave unexpected results. The paper ends with illustrative examples of the use of protecting groups in modern synthetic carbohydrate chemistry, namely the synthesis of nitrogen containing compounds belonging to an important class of polyhydroxylated cyclic amines. Compounds of this class are potent inhibitors of glycosidase enzymes.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Subject):
CarbohydratesCiting Articles
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
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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 ...
Use of Protecting Groups in Carbohydrate Chemistry: An Advanced Organic Synthesis Experiment
Anna C. Cunha , Leticia O. R. Pereira , Maria Cecília B. V. de Souza and Vitor F. FerreiraJournal of Chemical Education1999 76 (1), 79Use of Protecting Groups in Carbohydrate Chemistry: An Advanced Organic Synthesis Experiment
Anna C. Cunha , Leticia O. R. Pereira , Maria Cecília B. V. de Souza and Vitor F. FerreiraJournal of Chemical Education1999 76 (1), 79A 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 ...
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- Received: August 03, 2009
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