Polycations. 17. Synthesis and properties of polycationic derivatives of carbohydrates

N,N,N-Trimethyl-N-(methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosid-5-yl)ammonium 4-methylbenzenesulfonate sesquihydrate

“…Recent years have witnessed a resurgence of interest in the synthesis of QACs, especially their sugar derivatives, which have potential biological properties (Abel et al, 2002;Blizzard et al, 2002;Honda et al, 1988;Thomas et al, 2009;Maslov et al, 2010).…”

“…For QAC sugar derivatives, see: Abel et al (2002); Blizzard et al (2002); Honda et al (1988); Thomas et al (2009) ;Maslov et al (2010); Dmochowska et al (2006Dmochowska et al ( , 2009Dmochowska et al ( , 2011Pellowska-Januszek et al (2004); Skorupa et al (2004). For related synthetic methods, see: Gosh & Liu (1996); Sairam et al 2003; Sarabia-Garcia & Lopez-Herrera (1996); Dibrov et al (2010).…”

Self-assembling systems based on quaternized derivatives of 1,4-diazabicyclo[2.2.2]octane in nutrient broth as antimicrobial agents and carriers for hydrophobic drugs

“…Among known CSs, quaternized derivatives of 1,4-diazabicyclo[2.2.2]octane (DABCO) were selected for the present work, because of their wide applications [45][46][47] including their use as antibacterial agents [48,49]. We have previously shown that monoquaternized derivatives of 1,4-diazabicyclo[2.2.2]octane (DABCO-R, where R = n-C 12 H 25 , n-C 14 H 29 , n-C 16 H 33 , n-C 18 H 37 ,) demonstrated the high degree of both antibacterial and fungicidal activity [50].…”

Glycoside-Based Ionic Liquids

“…Tosyl chloride, in early efforts allowed to react in pyridine solution with hydroxylic substrates, reacts selectively with primary hydroxylic sites under aqueous conditions reminiscent of the simple Schotten-Baumann procedure for ester formation (Frantz et al 2002), as has been used for a wide range of ester preparations. The selectivity of the tosylation reaction and the ability to perform it in aqueous medium (Thomas et al 2009a) provide major advantages to this procedure, allowing facile formation of the tosylate ester and the equally facile subsequent displacement of the tosylate leaving group by an incoming tertiary amine nucleophile. Using the simple approach of selective tosylation of primary hydroxyl sites followed by nucleophilic substitution by a tertiary amine reagent, quaternary ammonium salts of a wide range of structures derived from carbohydrate precursors have been prepared.…”

“…Owing to the size of the cationic portion and the wealth of associated anionic species in a multitude of possible locations relative to the individual cationic sites, the possibilities of cationic carbohydrate derivatives for serving in ionic liquids are quite sizable. In this regard a series of polyhydroxylic polyammonium species have been prepared, derived from carbohydrate precursors (Thomas et al 2009a) and ionic liquids generated from them using phosphate and tosylate anions (Engel et al 2007). Of particular note are the syntheses of chiral tosylate associated ionic liquids derived from methyl α-Dglucopyranoside and mannose, as illustrated in Figure 5.…”