Bande, Omprakash P. ; Jadhav, Vrushali H. ; Puranik, Vedavati G. ; Dhavale, Dilip D. ; Lombardo, Marco (2009) Stereo-controlled approach to pyrrolidine iminosugar C-glycosides and 1,4-dideoxy-1,4-imino-l-allitol using a D-mannose-derived cyclic nitrone Tetrahedron Letters, 50 (49). pp. 6906-6908. ISSN 0040-4039
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2009.09.139
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 a-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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Cyclic Nitrone; Iminosugars; Enzyme Inhibitors; Pyrrolidine |
| ID Code: | 9726 |
| Deposited On: | 02 Nov 2010 10:52 |
| Last Modified: | 31 May 2011 11:49 |
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