4.4 Article

Efficient synthesis of kaempferol 3,7-O-bisglycosides via successive glycosylation with glycosyl ortho-alkynylbenzoates and trifluoroacetimidates

Journal

TETRAHEDRON LETTERS
Volume 53, Issue 22, Pages 2773-2776

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.03.103

Keywords

Selective glycosylation; Kaempferol; Glycosyl ortho-alkynylbenzoate; Glycosyl trifluoroacetimidate

Funding

  1. National Major Project of China [2009ZX09311-001, 2008ZXJ09004-007]
  2. National Natural Science Foundation of China [20921091, 20621062]

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Selective glycosylation of the 3-OH of 5,4'-di-O-acetyl-kaempferol was achieved with glycosyl orthoalkynylbenzoates as donors under the catalysis of Ph(3)PALINTf(2), and subsequent glycosylation of the remaining 7-OH with glycosyl trifluoroacetimidates under the catalysis of BF3.OEt2, after global deprotection, afforded the kaempferol 3,7-O-bisglycosides conveniently. (C) 2012 Elsevier Ltd. All rights reserved.

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