Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Acetyl Chloride-mediated Mild and Chemoselective Attachment and Removal of Tetrahydropyranyl (THP) Group

  • Yeom, Chang-Eun (Department of Chemistry, College of Natural Sciences, Seoul National University) ;
  • Shin, Yong-Je (Department of Chemistry, College of Natural Sciences, Seoul National University) ;
  • Kim, B.-Moon (Department of Chemistry, College of Natural Sciences, Seoul National University)
  • Published : 2007.01.20
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Abstract

A mild, chemoselective and convenient method for the formation and deprotection of tetrahydropyranyl ethers is described. With 1-5 mol% of acetyl chloride and slightly excess dihydropyran in methylene chloride or in neat dihydropyran, the formation of THP ethers from the corresponding alcohols was accomplished in the presence of many acid-sensitive functional groups. Efficient cleavage of THP ethers was also accomplished with the same reagent by switching the solvent to methanol.

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