Tandem Benzylic Oxidation/Dihydroxylation of α-Vinyl- and α-Alkenylbenzyl Alcohols
A de novo tandem benzylic oxidative dihydroxylation of α-vinyl- and α-alkenylbenzyl alcohols has been developed to give α,β-dihydroxypropiophenones (=2,3-dihydroxy-1-phenylpropan-1-ones) and α,β-dihydroxyalkyl phenones. This method was shown to be substrate-selective and specific for the oxidation of benzylic alcohols.
Fernandes, Rodney A.,Kattanguru, Pullaiah
p. 92 - 107
(2015/10/19)
Carbohydrate-carbohydrate interactions in water with glycophanes as model systems
The synthesis and conformational properties of glycophanes 2 and 3 (cyclodextrin-cyclophane hybrid receptors containing two maltose units linked by (4-hydroxymethyl) benzoic acid spacer) are described. The binding properties in water of these receptors with a series of 4-nitrophenyl glycosides with α- and β-configurations at the anomeric center have been studied using 1H NMR spectroscopy and molecular mechanics calculations. A comparison of these properties with those of glycophane 1 (an α,α-trehalose containing glycophane) and α-cyclodextrin (αCD) using the same glycosides shows the existence of a stabilizing contribution to the free energy of binding in the case of of glycophanes but not in the case of the αCD system. This contribution is due to carbohydrate-carbohydrate interactions between both host and guest lipophilic sugar surfaces. Glycophanes 1, 2, and 3 show similar α/β selectivity on binding the ligands, despite the great flexibility of 3 related to 1 and 2. Parallels are drawn between the thermodynamic behavior of these model systems and that proposed for sugar- protein interactions.
Morales, Juan Carlos,Zurita, Dacil,Penades, Soledad
p. 9212 - 9222
(2007/10/03)
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