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Synlett 1999; 1999(10): 1627-1629
DOI: 10.1055/s-1999-12529
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Highly Efficient β-Glucosylation of the Acidic Hydroxyl Groups, Phenol and Carboxylic Acid, with an Peracetylated Glucosyl Fluoride Using a Combination of BF3 · Et2O and DTBMP as a Promoter

Kin-ichi Oyama* , Tadao Kondo
  • *Chemical Instrument Center, Nagoya University, Chikusa, Nagoya 464-8602, Japan; Fax + 81-52-7 89-30 62; E-mail: tkmail@cic.nagoya-u.ac.jp
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Publication Date:
31 December 1999 (online)

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A combination of BF3 · Et2O and DTBMP was established to be an efficient promoter of β-glucosylation of both phenols and carboxylic acids with a peracetylated glycosyl fluoride (2). This new method achieved remarkably high yields and β-selectivity.

phenyl glucoside - 1-acylglucose - BF3 · Et2O - 2,6-di-tert-butyl-4-methylpyridine - peracetylated glucosyl fluoride