Reaction kinetics and mechanism of acid-catalyzed anomerization of 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranose

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The mechanism of the acid-catalyzed anomerization of 1-O-acetyl-2,3,5-O-benzoyi-alpha- and -beta-L-ribofuranoses in different acetic acid-acetic anhydride mixtures was investigated. The progress of the reactions was followed by NMR spectroscopy and the rate constants for the reactions were determined by the use of a kinetic model. The site of anomeric activation was clarified by the use of (13)C-labeled acetic acid and acetic anhydride, respectively, proving that the anomerization takes place by exocyclic C-O cleavage, thus ruling out anomerization via acyclic intermediates. The role of the acetyl cation as the catalytically active species was further verified. (C) 2009 Elsevier Ltd. All rights reserved.
Original languageUndefined/Unknown
Pages (from-to)1102–1109
Number of pages8
JournalCarbohydrate Research
Issue number9
Publication statusPublished - 2009
MoE publication typeA1 Journal article-refereed


  • (13)C Labeling
  • Anomerization
  • L-Ribose
  • Reaction kinetics

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