Glycosides nitro, synthesis

H. M. I. Osborn and A. Turkson, Synthesis and NMR spectroscopic analysis of 3-nitro-pyranoside, 3-nitro-septanoside and 4-nitro-septanoside derivatives by condensation of the anion of nitromethane with glycoside dialdehydes, Tetrahedron Asymmetry, 20 (2009) 2162-2166. 

Vasella has applied the concept of anomeric anion stabilization by a nitro group to the /3-D-JV-acetyl-D-glucosamine derivative 177, available in four steps from N-acetyl-n-glucosamine [52] (Scheme 39). Reaction of the tetraethylammonium nitronate derived from 177 with aldehyde 178 provides anti-179 which then undergoes stereoselectively reduction (see Sect. 2.2.1) to provide -C-glycoside 180, intermediate in a synthesis of N-acetyl-neuraminic acid. 

F. Baumberger and A. Vasella, Deoxynitrosugars—stereoelectronic control in the reductive denitration of tertiary nitro ethers. A synthesis of C-glycosides, Helv. Chim. Acta <56 221C (1983). 

J. Das and R. R. Schmidt, Convenient glycoside synthesis of amino sugars Michael-type addition to 2-nitro-D-galactal, Eur. J. Org. Chem., (1998) 1609-1613. 

Helferich reported that mercuric cyanide is sometimes superior to silver carbonate as base in the synthesis of glycosides and disaccharides. Thus the condensation of tetra-O-benzoylbromoglucose (1 equiv.) with benzyl alcohol (1 equiv.) in nitro-methane in the presence of mercuric cyanide (1 equiv.) gives tetra-O-benzoylbenzyl-/3-D-glucose in 90% yield. Zorbach used this general procedure, except that 1,2-dichloroethane was used as the solvent, in a successful synthesis of the cardiac-active... 

DAG 652 and 178, but also their ribofuranosides were capable of inhibiting nucleic add synthesis. iV- -D-ribofuranosides and other glycosides of unsubstituted IbPs and IcPs, as well as their halo and nitro derivatives act similarly but less efficiently. For example, 3- -D-ribofuranosyl-IbP inhibits the reproduction of Ranikhet disease virus and shows to some extent an anticancer activity. However, the aglycone of IbP also shows definite activity towards E. coli phage. But 3- -D-ribofuranosyl-IcP does not possess any activity (63IJC30). 6-Bromo-IbP, its 2-methyl derivative, as well as... 

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