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Synlett 2000; 2000(11): 1634-1636
DOI: 10.1055/s-2000-7942
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Regioselective Deprotection of Tert-Butyldimethylsilyl Ethers by Boron Trichloride

Yu-Ying Yang* , Wen-Bin Yang, Chin-Fen Teo, Chun-Hung Lin
  • *Institute of Biological Chemistry, Academia Sinica No. 128, Academia Road Section 2, Nan-Kang, Taipei, 11529-46, Taiwan; Fax +8 86-2-26 51-47 05; E-mail: chunhung@gate.sinica.edu.tw
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Publication Date:
31 December 2000 (online)

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Several fully tert-butyldimethylsilyl protected monosaccharides reacted with boron trichloride in tetrahydrofuran to effect a regioselective cleavage at the sites of primary alcohols. An application of this methodology was illustrated in an efficient approach to the synthesis of l-gulose from d-gluconolactone.

boron trichloride - regioselectivity - lactones - tert-butyldimethylsilyl ether - deprotection