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Glycoscience pp 179–225Cite as

Oxidation, Reduction, and Deoxygenation

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Abstract

In this chapter, methods for oxidation, reduction, and deoxygenation of carbohydrates are presented. In most cases, the reactions have been used on aldoses and their derivatives including glycosides, uronic acids, glycals, and other unsaturated monosaccharides. A number of reactions have also been applied to aldonolactones. The methods include both chemical and enzymatic procedures and some of these can be applied for regioselective transformation of unprotected or partially protected carbohydrates.

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Abbreviations

AIBN:

2,2′-azobisisobutyronitrile

BSTFA:

bis(trimethylsilyl)trifluoroacetamide

CAN:

ceric ammonium nitrate

DCC:

N,N′-dicyclohexylcarbodiimide

DIBALH:

diisobutylaluminum hydride

DMF:

dimethylformamide

DMSO:

dimethyl sulfoxide

HMPA:

hexamethylphosphoric triamide

MS:

molecular sieves

m-CPBA:

m-chloroperoxybenzoic acid

NBS:

N‑bromosuccinimide

NIS:

N‑iodosuccinimide

NMO:

N‑methyl‐morpholine N-oxide

PCC:

pyridinium chlorochromate

PDC:

pyridinium dichromate

TFAA:

trifluoroacetic anhydride

TEMPO:

2,2,6,6‑tetramethyl-1‑piperidinyloxy

TPAP:

tetrapropylammonium perruthenate

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Acknowledgement

The author thanks the Lundbeck Foundation for financial support. The Center for Sustainable and Green Chemistry is sponsored by the Danish National Research Foundation.

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Authors and Affiliations

  1. Department of Chemistry, Center for Sustainable and Green Chemistry, Technical University of Denmark, Lyngby, 2800, Denmark

    Robert Madsen

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  1. Robert Madsen
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Editors and Affiliations

  1. Natural Products and Glycotechnology Research Institute Inc., North Caroline State University, 4118 Swarthmore Road, Durham, NC, 27707, USA

    Bertram O. Fraser-Reid Prof. Dr.

  2. University Graduate School of Science and Engineering, 3-4-1 Ohkubo, Shinjuku, Tokyo, Japan

    Kuniaki Tatsuta Prof. Dr.

  3. Faculty of ScienceDepartment of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Joachim Thiem Prof. Dr.

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Madsen, R. (2008). Oxidation, Reduction, and Deoxygenation. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_4

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