1,4,6-Tri-O-acetyl-2,3-O-carbonyl-a-D-mannopyranose - CAS 53958-20-6
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CAS 53958-20-6 1,4,6-Tri-O-acetyl-2,3-O-carbonyl-a-D-mannopyranose

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1.Liver-targeted prodrugs of 2'-C-methyladenosine for therapy of hepatitis C virus infection.
Hecker SJ1, Reddy KR, van Poelje PD, Sun Z, Huang W, Varkhedkar V, Reddy MV, Fujitaki JM, Olsen DB, Koeplinger KA, Boyer SH, Linemeyer DL, MacCoss M, Erion MD. J Med Chem. 2007 Aug 9;50(16):3891-6. Epub 2007 Jul 18.
2'-C-Methyladenosine exhibits impressive inhibitory activity in the cell-based hepatitis C virus (HCV) subgenomic replicon assay, by virtue of intracellular conversion to the corresponding nucleoside triphosphate (NTP) and inhibition of NS5B RNA-dependent RNA polymerase (RdRp). However, rapid degradation by adenosine deaminase (ADA) limits its overall therapeutic potential. To reduce ADA-mediated deamination, we prepared cyclic 1-aryl-1,3-propanyl prodrugs of the corresponding nucleoside monophosphate (NMP), anticipating cytochrome P450 3A-mediated oxidative cleavage to the NMP in hepatocytes. Lead compounds identified in a primary rat hepatocyte screen were shown to result in liver levels of NTP predictive of efficacy after intravenous dosing to rats. The oral bioavailability of the initial lead was below 5%; therefore, additional analogues were synthesized and screened for liver NTP levels after oral administration to rats. Addition of a 2',3'-carbonate prodrug moiety proved to be a successful strategy, and the 1-(4-pyridyl)-1,3-propanyl prodrug containing a 2',3'-carbonate moiety displayed oral bioavailability of 39%.
2.Controlled formation and topologies of thiophenolate-based macrocycles: rings, cylinders and bowls.
Christensen A1, Mayer C, Jensen F, Bond AD, McKenzie CJ. Dalton Trans. 2006 Jan 7;(1):108-20. Epub 2005 Nov 7.
The Schiff-base condensations of 1,3-diaminopropane with a protected thiophenol dialdehyde in the presence of Ni(2+), Pd(2+) or Zn(2+) can be controlled to yield either mononuclear acyclic, or 2 + 2 and 4 + 4 macrocyclic complexes by the choice of both metal cation and counteranion. The Ni(2+) complex of the 2 + 2 macrocycle contains two square-planar nickel ions and shows an arrangement similar to one observed previously: the mu-S atoms of the thiophenolate groups are pyramidal and lie on the same side of the plane defined by the four N atoms of the macrocycle to give a V-shaped molecule. By contrast, the Zn(2+) complex of the 2 + 2 macrocycle undergoes oligomerization to yield a bowl-shaped hexanuclear complex that includes a mu(3)-carbonate anion. Essential for this topology is the presence of three mu(3)-S-thiophenolato groups that link the three macrocyclic units to form a Zn(3)S(3) ring that seals the bottom part of the bowl. In this arrangement, one of the pyramidal mu(3)-S atoms in each dinuclear Zn(2+) complex is inverted relative to the arrangement observed for the dinickel complexes.
3.Regiospecific anomerisation of acylated glycosyl azides and benzoylated disaccharides by using TiCl4.
Farrell M1, Zhou J, Murphy PV. Chemistry. 2013 Oct 25;19(44):14836-51. doi: 10.1002/chem.201302572. Epub 2013 Sep 20.
Chelation induced anomerisation is promoted when Lewis acids, such as TiCl4 or SnCl4, coordinate to the pyranose ring oxygen atom and another site, giving rise to endocyclic cleavage and isomerisation to the more stable anomer. In this research regiospecific site-directed anomerisation is demonstrated. TiCl4 (2.5 equiv) was employed to induce anomerisation of 15 glycosyl azide and disaccharide substrates of low reactivity, and high yields (>75%) and stereoselectivies (α/β>9:1) were achieved. The examples included glucopyranuronate, galactopyranuronate and mannopyranuronate as well as N-acetylated glucopyranuronate and galactopyranuronate derivatives. A disaccharide with the α1→4 linkage found in polygalacturonan was included. The use of benzoylated saccharides was found to be important in disaccharide anomerisation as attempts to isomerise related acetyl protected and 2,3-carbonate protected derivatives were not successful.