Bulletin of the Korean Chemical Society

  • 제28권1호
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  • Pages.103-107
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  • 2007
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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)
  • 발행 : 2007.01.20
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초록

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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  4. Acetyl Chloride-Mediated Mild and Chemoselective Attachment and Removal of Tetrahydropyranyl (THP) Group. vol.38, pp.21, 2007, https://doi.org/10.1002/chin.200721042
  5. Tetrahydropyranyl ether (THPE) formation in hydroxyl group protection and conversion to other useful functionalities vol.4, pp.40, 2007, https://doi.org/10.1039/c4ra02093f