Pandey, Ganesh ; Kapur, Manmohan (2001) A novel approach to both the enantiomers of potent glycosidase inhibitor isofagomine via PET-promoted cyclization of 1-[Benzyl(trimethylsilyl-methyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-threo-pent-4-ynitol Synlett, 8 . pp. 1263-1267. ISSN 0936-5214
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Official URL: https://www.thieme-connect.com/ejournals/abstract/...
Related URL: http://dx.doi.org/10.1055/s-2001-15063
Abstract
The cyclization of PET-generated α-trimethylsilylmethylamine radical cation to a tethered acetylene moiety has been exploited to solve the problem of the generation of an aminomethyl group next to a stereocenter in the synthesis of 1-N-iminosugar type glycosidase inhibitors. Its success is demonstrated by the synthesis of (+)- as well as (-)-isofagomine, an extremely potent β -glucosidase inhibitor of the 1-N-iminosugar class.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Thieme Medical Publishers. |
| Keywords: | Photoinduced Electron Transfer (PET); α-trimethylsilylmethylamine Radical Cation; Glycosidase Inhibitors; 1-N-iminosugars; Isofagomine |
| ID Code: | 61006 |
| Deposited On: | 13 Sep 2011 11:29 |
| Last Modified: | 13 Sep 2011 11:29 |
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