Synthesis and L-fucosidase inhibitory potency of a cyclic sugar imine and its pyrrolidine analogue

The synthesis of a fully deprotected ketimine-type iminosugar is reported, starting from commercial D-mannose diacetonide. An appropriate solvent system was critical for the success of the key tandem addition/cyclization reaction. Reduction of the imine was also achieved to yield the corresponding pyrrolidine in a stereoselective manner. The cyclic sugar imine displayed modest fucosidase inhibitory activity when compared to the saturated analogue. (C) 2008 Elsevier Ltd. All rights reserved.


Published in:
Tetrahedron-Asymmetry, 19, 1829-1832
Year:
2008
Keywords:
Laboratories:




 Record created 2010-11-30, last modified 2018-12-03


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