Stereo-controlled approach to pyrrolidine iminosugar C-glycosides and 1,4-dideoxy-1,4-imino-l-allitol using a d-mannose-derived cyclic nitrone |
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Authors: | Omprakash P Bande Vrushali H Jadhav Vedavati G Puranik Dilip D Dhavale Marco Lombardo |
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Institution: | aDepartment of Chemistry, Garware Research Centre, University of Pune, Pune 411 007, India;bCentre for Material Characterization, National Chemical Laboratory, Pune 411 008, India;cDipartimento di Chimica ‘G. Ciamician’, Università di Bologna, via Selmi 2, 40126 Bologna, Italy |
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Abstract: | Intramolecular N-alkylation of 2,3-O-isopropylidene-5-O-methanesulfonyl-6-O-t-butyldimethylsilyl-d-mannofuranose-oxime 7 afforded a five-membered cyclic nitrone 9, which on N–O bond reductive cleavage followed by deprotection of –OTBS and acetonide functionalities gave 1,4-dideoxy-1,4-imino-l-allitol (DIA) 3. Addition of allylmagnesium chloride to nitrone 9 afforded α-allylated product 10a in high diastereoselectivity providing an easy entry to N-hydroxy-C1-α-allyl-substituted pyrrolidine iminosugar 4a after removal of protecting group, while N–O bond reductive cleavage in 10a afforded C1-α-allyl-pyrrolidine iminosugar 4b. |
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Keywords: | Cyclic nitrone Iminosugars Enzyme inhibitors Pyrrolidine |
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