A general method for the synthesis of C-glycosides of nojirimycin

Fuchss, Thomas, Streicher, Hansjorg and Schmidt, Richard R (1997) A general method for the synthesis of C-glycosides of nojirimycin. LIEBIGS ANNALEN-RECUEIL (7). pp. 1315-1321. ISSN 0947-3440

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Abstract

Methyl 2,3,4,6-tetra-O-acetyl-N-(benzyloxycarbonyl)nojirimycin (3) can be readily transformed into the corresponding azaglycal 6 or fluoride 7, which are versatile glycosyl/piperidinosyl donors. Reaction of 7 with allyltrimethylsilane, propinyltrimethylsilane, trimethylsilyl cyanide, and trimethylsilyl enol ether as carbon nucleophiles, afforded, in the presence of BF3 . OEt2 as catalyst, the corresponding C-glycosides 8-10 and 12-14 in good yields. The anomeric configurations of the C-glycosides are ascertained with the help of ROESY-NMR data.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Hans Streicher
Date Deposited: 06 Feb 2012 18:27
Last Modified: 16 Mar 2012 17:15
URI: http://sro.sussex.ac.uk/id/eprint/16464
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