13070-29-6Relevant academic research and scientific papers
De novo synthesis and lectin binding studies of unsaturated carba-pyranoses
Leermann, Timo,Block, Oliver,Podeschwa, Michael A. L.,Pfueller, Uwe,Altenbach, Hans-Josef
, p. 3965 - 3974 (2010)
Starting from branched para-benzoquinones a practical and highly flexible route is described for the preparation of unsaturated carbapyranoses. The potential of the synthesized galactose analogues to act as competitive inhibitors in lectin-carbohydrate interactions is investigated by means of Surface Plasmon Resonance (SPR) Spectroscopy.
A novel and stereoselective synthesis of 2-bromo-6-chloro-5-methylcyclohex-4-ene-1,3-diyl diacetate: conduritol-A derivative
Kelebekli, Latif,Kaplan, Dilek
, p. 803 - 808 (2019/12/27)
The stereoselective synthesis of 2-bromo-6-chloro-5-methylcyclohex-4-ene-1,3-diyl diacetate, methyl-substituted dihaloconduritol-A is reported. Bromination of 2-methylbenzo-1,4-quinone followed by the reduction in the carbonyl groups with NaBH4 to give a dioldibromo compound. The diol was converted to diacetates by acetylation with Ac2O-pyridine. Reaction of methyl-dioldibromodiacetate with LiOH gave stereoselectively the monoepoxide compound. Controlled reaction of the epoxide with AcCl in methylene chloride furnished the desired new dihaloconduritol-A derivative which was characterized by spectroscopic methods. All the synthesized compounds were characterized by FT-IR, 1H-NMR, 13C-NMR, COSY (2D-NMR), and HRMS analyses.
Stereospecific synthesis of novel methyl-substituted mono- and di-methoxy conduritols
Kelebekli, Latif,Kaplan, Dilek
, p. 8 - 13 (2016/12/09)
Methyl-monomethoxy conduritol-B and methyl-dimethoxy conduritol-B were synthesized starting from 2-methylbenzo-1,4-quinone. Bromination of 2-methylbenzo-1,4-quinone was followed by the reduction of the carbonyl groups with NaBH4to give a dioldibromo compound. Methyl-dimethoxy conduritol-B was synthesized from the reaction of the dioldibromo compound with CH3ONa, followed by acetylation with Ac2O-pyridine to obtain methyl-dimethoxy diacetate. On the other hand, acetylation of the methyl-dioldibromo compound followed by reaction with LiOH gave a monoepoxide compound stereoselectively. The reaction of the epoxide with H+/Ac2O afforded the monobromo triacetate. Controlled reaction of monobromo-triacetate with CH3ONa in MeOH furnished the desired new methyl-monomethoxy conduritol-B. The structures of all synthesized compounds were characterized by spectroscopic methods.
