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Essentials of Carbohydrate Chemistry

Part of the book series: Springer Advanced Texts in Chemistry ((SATC))

Abstract

Carbohydrates are polyhydroxy aldehydes or ketones. Therefore, one of their primary chemical properties is that of a polyalcohol. It is natural then that one of the first types of derivatives to be formed was esters. The formation of a completely acetylated carbohydrate can be obtained by the reaction with acetic anhydride in the presence of either a basic or an acidic catalyst. When reducing carbohydrates react with acetic anhydride in the presence of sodium acetate at 4°C, the ßanomer is favored (reactions 4.1 and 4.2).

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Abbreviations

Ac:

acetyl

Ac2O:

acetic anhydride

AcOH:

acetic acid

Bn:

benzyl

Bu:

butyl

Bz:

benzoyl

DAST:

diethylaminosulfur triflouride

DMF:

dimethylformamide

DMSO:

dimethylsulfoxide

HMPA:

hexamethyl phosphoramide

Me:

methyl

Ph:

phenyl

Ph3P:

triphenylphosphine

Pv:

pivaloyl (trimethyl acetyl)

Ra Ni:

Raney nickel

Tf:

trifyl (trifluoromethyl sulfonyl)

Tf2O:

trifylic anhydride (trifluoromethylsulfonyl anhydride)

THF:

tetrahydrofuran

Tr:

trityl (triphenyl methyl)

Ts:

tosyl (p-toluene sulfonyl)

TsOH:

tosic acid

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  1. Laboratory of Carbohydrate Chemistry and Enzymology Department of Biochemistry and Biophysics, Iowas State University, Ames, IA, 50011, USA

    John F. Robyt

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© 1998 Springer Science+Business Media New York

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Robyt, J.F. (1998). Modifications. In: Essentials of Carbohydrate Chemistry. Springer Advanced Texts in Chemistry. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-1622-3_4

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  • DOI: https://doi.org/10.1007/978-1-4612-1622-3_4

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  • Print ISBN: 978-1-4612-7220-5

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