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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 1
BKCSDE 28(1)
January 20, 2007 

Acetyl Chloride-mediated Mild and Chemoselective Attachment and Removal of Tetrahydropyranyl (THP) Group
Chang-Eun Yeom, Yong Je Shin, B. Moon Kim*
THP ether, Protecting group, Chemoselective, Tetrahydropyranylation, Detetrahydropyranylation
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.
103 - 107
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