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Synlett 1996; 1996(12): 1179-1180
DOI: 10.1055/s-1996-5724
DOI: 10.1055/s-1996-5724
letter
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Regioselective Reductive Opening of 4,6-O-Benzylidene Acetals of Glucose or Glucosamine Derivatives by BH3⋅Me2NH - BF3⋅OEt2
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
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