4.5 Article

Synthesis of fructofuranosides: efficient glycosylation with N-phenyltrifluoroacetimidate as the leaving group

Journal

CARBOHYDRATE RESEARCH
Volume 343, Issue 17, Pages 2992-2996

Publisher

ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2008.09.001

Keywords

Fructosylation; Trifluoroacetimidate; Glycosyl donor

Funding

  1. National Natural Science Foundation of China [29925203]
  2. Committee of Science and Technology of Shanghai [02QMA1401]

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Fructofuranosyl trifluoroacetimidate 3 was demonstrated to be an effective glycosyl donor that exhibited good alpha-selectivity and good yield in fructosylation reactions. The reaction proceeds via neighboring group participation, which was proved by the isolation of a stable allylic orthoester intermediate. (C) 2008 Elsevier Ltd. All rights reserved.

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