TITLE

Lanthanum-catalyzed aqueous acylation of monosaccharides by benzoyl methyl phosphate

AUTHOR(S)
Gray, Ian James; Ren, Rui; Westermann, Bernhard; Kluger, Ronald
PUB. DATE
April 2006
SOURCE
Canadian Journal of Chemistry;Apr2006, Vol. 84 Issue 4, p620
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
It was previously reported that diols dissolved in water (pH 8, EPPS buffer) react with benzoyl methyl phosphate (BMP) in the presence of lanthanide ions to form monobenzoyl esters. We have investigated the possibility of extending this process to include formation of esters of monosaccharides in water from lanthanide-catlayzed reactions with BMP. The combination of methyl-α-D-glucopyranoside and BMP in the presence of lanthanum trichloride gave selective monoacylation of the 2- and 6-hydroxyl groups in a ratio of 2:1. The likely mechanism involves preferential bisbidentate coordination of BMP and the diol to lanthanide ion (which explains how an ester forms when water is in enormous excess) followed by base-catalyzed intramolecular acyl transfer. The method should be generally applicable where a selective acylation reaction in water as solvent is desirable.
ACCESSION #
21197095

 

Related Articles

  • Sorption des ions chromate sur une hydrotalcite de synthèse calcinée. Bakhti, Abdellah; Ouali, Mohand Saïd // Water Quality Research Journal of Canada (Canadian Association o;2005, Vol. 40 Issue 2, p177 

    We examined the way that chromate ions are held by a synthetic hydrotalcite (Mg-Al-CO₃) and its calcination product at 550°C. We used several physico-chemical methods of analysis (X-ray powder diffraction, thermal analysis and chemical composition) to determine the chemical formula of...

  • Gadolinium blocks proton-activated currents in isolated Purkinje cells. I. Sharonova; A. Dvorzhak; V. Vorobjov // Bulletin of Experimental Biology & Medicine;Mar2008, Vol. 145 Issue 3, p307 

    Abstract  Patch-clamp and concentration jump studies showed that gadolinium ions dose-dependently reduced the amplitude of proton-activated currents (pH 6.5) in isolated Purkinje cells (gadolinium concentration producing a half-maximum effect was 69 µM for the peak and 8 µM for the...

  • O-nucleophilic features of amidoximes in acyl group transfer reactions. Prokop'eva, T. M.; Simanenko, Yu. S.; Karpichev, E. A.; Savelova, V. A.; Popov, A. F. // Russian Journal of Organic Chemistry;Nov2004, Vol. 40 Issue 11, p1617 

    Analysis of kinetic behavior of isomericZ-amidoximes and theirZ-ions in reactions with 4-nitrophenyl-4-toluenesulfonate, diethylphosphate, and diethylphosphonate was performed in the framework of Bronsted relationship. The reactivity of amidoximate anions with respect to the mentioned substrates...

  • Sinergetic membrane extraction of lithium ions with new organophosphorus carriers. Garifzyanov, A.; Davletshina, N.; Garipova, A.; Cherkasov, R. // Russian Journal of General Chemistry;Feb2014, Vol. 84 Issue 2, p285 

    We have studied membrane transport properties towards alkali metal ions of sinergetic mixtures of organophosphorus carries, N,N-bis(dihexylphosphorylmethyl)octylamine and didecylthiophosphorus or didecyldithiophosphorus acids. The influence of main parameters of extraction (pH of the feed phase...

  • A Ternary Complex of Vanadium(V) with 4-(2-Pyridylazo)-resorcinol and Thiazolyl Blue and its Application. Gavazov, Kiril; Lekova, Vanya; Patronov, Georgi // Acta Chimica Slovenica;2006, Vol. 53 Issue 4, p506 

    A new ternary complex of vanadium(V) with 4-(2-pyridylazo)-resorcinol (PAR) and thiazolyl blue (MTT) has been obtained and studied by using an extraction-spectrophotometric method. The complex absorbs light at 560 nm with a molar absorptivity coefficient of 3.84x104 L mol-1 cm-1 at the optimum...

  • All-Solid-State PVC Membrane Ag+-Selective Electrodes Based on Diaza-18-Crown-6 Compounds. Isildak, Ibrahim; Yolcu, Murat; Isildak, Omer; Demirel, Nadir; Topal, Giray; Hosgoren, Halil // Microchimica Acta;Jan2004, Vol. 144 Issue 1-3, p177 

    Two diaza-crown ether compounds were synthesized and evaluated as Ag+-selective carriers in polyvinylchloride (PVC) membrane electrodes of solid-state type. The all-solid-state PVC membrane electrode based on N,N-Dibenzyl-dibenzo-diaza-18-crown-6 exhibited a super-Nernstian response (75±10 mV...

  • The extraction of Zn(II) in aqueous PEG (1550) -- (NH4)2SO4 two-phase system using Cl- ions as extracting agent. Bulgariu, Laura; Bulgariu, Dumitru // Journal of the Serbian Chemical Society;Mar2007, Vol. 72 Issue 3, p289 

    The extraction of Zn(II) in an aqueous PEG (1550) – (NH4)2SO4 two-phase system as a function of several experimental parameters was studied. PEG-based aqueous two-phase systems are composed of two immiscible phases: a polymer-rich phase and a salt-rich phase, which can be used for...

  • Development of Extractive Spectrophotometric Method for the Determination of Copper (II) with Isatin-3-Thiosemicarbazone (HITSC). Tamhane, Gauri P.; Barhate, V. D. // Asian Journal of Research in Chemistry;Mar2012, Vol. 5 Issue 3, p351 

    A simple extractive spectrophotometric method has been developed for the determination of Cu(II) by using Isatin - 3 - Thiosemicarbazone(HITSC) as an analytical reagent .HITSC has been synthesized and characterized by elemental and spectral analysis. HITSC extracts Cu(II)quantitatively (99.67%)...

  • Ion-Chromatographic Determination of Fluoride Ions in Atmospheric Precipitates and Natural Waters. Kalyakina, O. P.; Dolgonosov, A. M. // Journal of Analytical Chemistry;Oct2003, Vol. 58 Issue 10, p951 

    An ion-chromatographic method modernized to improve the selectivity and accuracy of analysis was used for determining fluoride ions in environmental samples. The method described was implemented on a domestic portable KhPI-1 ion chromatograph, which demonstrates the possibility of ecological...

Share

Read the Article

Courtesy of THE LIBRARY OF VIRGINIA

Sorry, but this item is not currently available from your library.

Try another library?
Sign out of this library

Other Topics