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Synlett 1996; 1996(12): 1179-1180
DOI: 10.1055/s-1996-5724
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Regioselective Reductive Opening of 4,6-O-Benzylidene Acetals of Glucose or Glucosamine Derivatives by BH3⋅Me2NH - BF3⋅OEt2

Masato Oikawa, Wen-Chi Liu, Yoshihiko Nakai, Shuhei Koshida, Koichi Fukase, Shoichi Kusumoto*
  • *Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560, Japan, Fax 81-6-850-5419, skus@chem.sci.osaka-u.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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Here described is the reduction of 4,6-O-benzylidene functionalities of D-glucose or D-glucosamine with various protecting groups by borane dimethylamine complex and boron trifluoride etherate. The 4-O-benzyl products were selectively obtained when the reaction was carried out in dichloromethane for substrates with 3-O-benzyl groups. In contrast, the reaction in acetonitrile provided the 6-O-benzyl products predominantly for substrates 3-O-protected in other forms than a benzyl ether.

borane dimethylamine complex - boron trifluoride etherate - selective reduction - benzylidene acetal - sugar derivative

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