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Synthesis 2001; 2001(4): 0555-0558
DOI: 10.1055/s-2001-12343
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A Novel and Chemoselective Transformation of Alcohol Silyl Ethers into the Corresponding Tetrahydropyranyl Ethers

Takeshi Suzuki* , Takeshi Oriyama
  • *Faculty of Science, Department of Environmental Sciences, Ibaraki University, 2-1-1 Bunkyo, Mito 310-8512, Japan; Fax + 81(29)2 28 84 06; E-mail: tor@mito.ipc.ibaraki.ac.jp
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Publication Date:
31 December 2001 (online)

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Direct conversion of alcohol silyl ethers into the corresponding tetrahydropyranyl (THP) ethers can be easily performed by reaction with THP acetate under the influence of a catalytic amount of tert-butyldimethylsilyl trifluoromethanesulfonate (TBSOTf). Aliphatic TBS ether can be selectively transformed into the corresponding THP ether in the presence of phenolic TBS ether.

silyl ether - THP ether - THP acetate - tert-butyldimethylsilyl trifluoromethanesulfonate - one-step conversion of protective group - chemoselectivity