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Synlett 1996; 1996(6): 523-525
DOI: 10.1055/s-1996-5497
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Convenient Methods for the Direct Conversion of Tetrahydropyranyl Ethers into Silyl-protected Alcohols and for the Removal of Tetrahydropyranyl Group

Takeshi Oriyama* , Kaori Yatabe, Satomi Sugawara, Yuko Machiguchi, Gen Koga
  • *Department of Chemistry, Faculty of Science, Ibaraki University, Bunkyo, Mito, 310, Japan
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Publication Date:
31 December 2000 (online)

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A reagent system of trialkylsilyl trifluoromethanesulfonate and triethylamine cleaves readily tetrahydropyranyl ethers to give directly the corresponding trialkylsilyl ethers in good yields under very mild conditions. Dialkylsilylene derivatives of 1,3-diol can be obtained directly from the corresponding bis-tetrahydropyranyl ethers of 1,3-diol. And furthermore, alcohol tetrahydropyranyl ethers can be easily deprotected by treatment of trimethylsilyl trifluoromethanesulfonate alone to afford parent free alcohols in good yields.

tetrahydropyranyl ether - trialkylsilyl ether - trialkylsilyl triflate - triethylamine - deprotection