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http://dx.doi.org/10.5012/bkcs.2007.28.1.103

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)
Publication Information
Bulletin of the Korean Chemical Society / v.28, no.1, 2007 , pp. 103-107 More about this Journal
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.
Keywords
THP ether; Protecting group; Chemoselective; Tetrahydropyranylation; Detetrahydropyranylation;
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