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
Synthesis and l-fucosidase inhibitory potency of a cyclic sugar imine and its pyrrolidine analogue / Behr, Jean-Bernard; Pearson, Morwenna S. M.; Bello, Claudia; Vogel, Pierre; Plantier-Royon, Richard. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - ELETTRONICO. - 19:(2008), pp. 1829-1832. [10.1016/j.tetasy.2008.06.019]
Synthesis and l-fucosidase inhibitory potency of a cyclic sugar imine and its pyrrolidine analogue
Bello, Claudia;
2008
Abstract
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
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