2,3,4,6-Tetra-O-acetyl-1-azido-1-deoxy-a-D-galactopyranosyl cyanide - CAS 168567-90-6
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1.Regioselective Acylation of Diols and Triols: The Cyanide Effect.
Peng P, Linseis M, Winter R, Schmidt RR. J Am Chem Soc. 2016 Apr 22. [Epub ahead of print]
Central topics of carbohydrate chemistry embrace structural modifications of carbohydrates and oligosaccharide synthesis. Both require regioselectively protected building blocks that are mainly available via indirect multistep procedures. Hence, direct protection methods targeting a specific hydroxy group are demanded. Dual hydrogen-bonding will eventually differentiate between differently positioned hydroxy groups. As cyanide is capable of various kinds of hydrogen-bonding and as it is a quite strong sterically non-demanding base, regioselective O-acylations should be possible at low temperatures even at sterically congested positions, thus permitting formation and also isolation of the kinetic product. Indeed, 1,2-cis-diols, having an equatorial and an axial hydroxy group, benzoyl cyanide or acetyl cyanide as acylating agent and DMAP as catalyst yield at -78 oC the thermodynamically unfavorable axial O-acylation product; acyl migration is not observed under these conditions.
2.Synthesis and x-ray crystallographic analysis of 4,6-di-O-acetyl-2,3-dideoxy-α-d-threo-hexopyranosyl cyanide.
Rotella M1, Giovine M1, Dougherty W Jr1, Boyko W1, Kassel S1, Giuliano R2. Carbohydr Res. 2016 Apr 29;425:40-2. doi: 10.1016/j.carres.2016.03.001. Epub 2016 Mar 9.
The glycopyranosyl cyanide 4,6-di-O-acetyl-2,3-dideoxy-α-d-threo-hexopyranosyl cyanide has been synthesized from tri-O-acetyl-d-galactal by reaction with trimethylsilyl cyanide in the presence of boron trifluoride diethyl etherate followed by catalytic hydrogenation. The synthesis provides the α-anomer stereoselectively, the structure of which was assigned based on 2D NMR techniques and x-ray crystallography.
3.Anodic oxidation of coke oven wastewater: Multiparameter optimization for simultaneous removal of cyanide, COD and phenol.
Sasidharan Pillai IM1, Gupta AK2. J Environ Manage. 2016 Jul 1;176:45-53. doi: 10.1016/j.jenvman.2016.03.021. Epub 2016 Mar 31.
Anodic oxidation of industrial wastewater from a coke oven plant having cyanide including thiocyanate (280 mg L(-1)), chemical oxygen demand (COD - 1520 mg L(-1)) and phenol (900 mg L(-1)) was carried out using a novel PbO2 anode. From univariate optimization study, low NaCl concentration, acidic pH, high current density and temperature were found beneficial for the oxidation. Multivariate optimization was performed with cyanide including thiocyanate, COD and phenol removal efficiencies as a function of changes in initial pH, NaCl concentration and current density using Box-Behnken experimental design. Optimization was performed for maximizing the removal efficiencies of these three parameters simultaneously. The optimum condition was obtained as initial pH 3.95, NaCl as 1 g L(-1) and current density of 6.7 mA cm(-2), for which the predicted removal efficiencies were 99.6%, 86.7% and 99.7% for cyanide including thiocyanate, COD and phenol respectively.
4.Cyanide Scavenging by a Cobalt Schiff-base Macrocycle: A Cost-effective Alternative to Corrinoids.
Lopez-Manzano E, Cronican AA, Frawley KL, Peterson J, Pearce LL. Chem Res Toxicol. 2016 Apr 22. [Epub ahead of print]
The complex of cobalt(II) with the ligand 2,12-dimethyl-3,7,11,17-tetraazabicyclo-[11.3.1]heptadeca-1(7)2,11,13,15-pentaene (CoN4[11.3.1]) has been shown to bind two molecules of cyanide in a cooperative fashion with an association constant of 2.7 (± 0.2) x 105. In vivo, irrespective of whether initially administered as the Co(II) or the Co(III) cation, EPR spectroscopic measurements on blood samples show that at physiological levels of reductant (principally ascorbate) CoN4[11.3.1] becomes quantitatively reduced to the Co(II) form. However, following addition of sodium cyanide, a dicyano Co(III) species is formed, both in blood and in buffered aqueous solution at neutral pH. In keeping with the other cobalt-containing cyanide-scavenging macrocycles cobinamide and cobalt(III) meso-tetra(4-N-methylpyridyl)porphine, we found that CoN4[11.3.1] exhibits rapid oxygen turnover in the presence of the physiological reductant ascorbate. This behavior could potentially render CoN4[11.
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CAS 168567-90-6 2,3,4,6-Tetra-O-acetyl-1-azido-1-deoxy-a-D-galactopyranosyl cyanide

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