13070-29-6Relevant articles and documents
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.
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.