4.4 Article

Chemoselective glycosylation of carboxylic acid with glycosyl ortho-hexynylbenzoates as donors

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 11, Pages 1504-1507

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.01.039

Keywords

Glycosylation; Chemoselective; Glycosyl ortho-hexynylbenzoate; Ester glycoside; Orthoester; PPh3AuOTf

Funding

  1. National Natural Science Foundation of China [90713003, 20621062]
  2. Ministry of Science and Technology of China [2009ZX09311-001]

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The gold(I)-catalyzed glycosylation of acid alcohols with glycosyl ortho-hexynylbenzoates in the presence of BF3 center dot Et2O and DBU provided the corresponding ester glycosides chemoselectively in high yield; while with DTBP as an additive instead, orthoester formation with the alcohol was effected selectively. (C) 2010 Elsevier Ltd. All rights reserved.

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