Allyl C-glycosidations of totally unprotected glycals and allyltrimethylsilane with trimethylsilyl trifluoromethanesulfonate (TMSOTf)

Kazunobu Toshima, Toru Ishizuka, Goh Matsuo, Masaya Nakata

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Allyl C-glycosidations of the totally unprotected glycals, L-rhamnal (1), D-glucal (2), D-galactal (3) and D-fucal (4), with allyltrimethylsilane (5) using TMSOTf proceeded much more effectively than those of the corresponding acetylated glycals 10∼13 to furnish the unprotected and 2,3-unsaturated allyl α-C-glycosides 6∼9 in high yields, respectively.

Original languageEnglish
Pages (from-to)5673-5676
Number of pages4
JournalTetrahedron Letters
Issue number31
Publication statusPublished - 1994 Aug 1


ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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