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With para-dodecylbenzenesulfonic acid; at 80.0℃; for 24.0h;Green chemistry;
General procedure: A typical reaction was carried out by adding 3.6 g (0.02 mol)glucose to a 100 ml glass reactor containing 0.2 mol of correspondingalcohol and 0.33 g (0.01 mol) dodecylbenzenesulfonic acid. The resultingsuspension was agitated intensively (700 rpm) at desired temperaturefor 24 h. After that the reaction mixture (clear liquid) was cooleddown to room temperature and analysed (GPC and GC/MS).
With almond meal; In water; at 50.0℃; for 168.0h;Enzymatic reaction;Thermodynamic data; Equilibrium constant;
General procedure: In a typical experiment, an alkyl alcohol was used as thesubstrate and the medium. The reaction mixture was composedof 18 ml of primary alcohol and 2 ml of water containing 0.25mol/L glucose (Scheme 1). After 60 mg almond meal wasadded, the mixture was incubated in a 100-ml flask and constantlyshaken at 180 r/min at 50 C. At certain intervals, 50 lof the mixture was withdrawn and analyzed by HPLC.For the synthesis of methyl -D-glucoside, 2 ml of methanol,16 ml of acetonitrile, and 2 ml of water containing 0.25 mol/Lglucose were mixed.
With almond meal; In water; at 50.0℃; for 168.0h;Thermodynamic data; Equilibrium constant;
General procedure: For the hydrolytic reaction of glucosides, 0.25 mol/L of propyl, hexyl, or octyl glucoside was dissolved in a mixture of18 ml of the corresponding alcohol and 2 ml of water containing60 mg almond meal. The reaction was performed in a100-ml flask that was constantly shaken at 180 r/min at 50 C.After the mixture was incubated for 72 and 144 h respectively,30 mg almond meal was supplemented. The reverse hydrolysisof the propyl, hexyl, and octyl glucosides was performed as inthe n-alkyl -D-glucosides synthesis.
N'-(β-D-glucopyranosyl)-p-toluenesulfonohydrazide[ No CAS ]
[ 29781-81-5 ]
[ 58846-77-8 ]
Yield
Reaction Conditions
Operation in experiment
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20.0℃; for 0.5h;Molecular sieve; Inert atmosphere;
General procedure: A mixture of GSH (0.718 mmol), dimethylformamide (5.0 mL),n-decanol (5, 10 or 20 equiv relative to GSH) and freshly-activated4 A molecular sieves was allowed to stir for 1 h under N2 before the addition of N-bromosuccinimide (0.307 g, 1.72 mmol).The reaction was stirred for 30 min when TLC analysis (20:80MeOH/CH2Cl2) indicated that the starting material had been consumed.Sufficient Amberlite IRA-67 free base resin was added toquench the reaction, as judged by its loss of yellow colouration.The mixture was filtered and the solvent removed under reducedpressure. The residue was purified by flash chromatography (8-15% MeOH in CH2Cl2 with 1% Et3N) to afford the target n-decyl-O-glycosides.
General procedure: The ester was prepared by reacting 0.095 mol of AG (dispersed in squalene) with citric acid anhydride dissolvedin acetic acid at 90 C for about 2 h with stirring. Theexcess acetic acid and acetic acid anhydride were removedby vacuum distillation. After the esterification step, thealkyl monoglucoside citric monoester was extracted fromthe mixture by adding 50 mL anhydrous ethanol. NaOH(50 % aqueous) was added to adjust the pH to 8 withconstantly stirring. The precipitated AG-EC was isolatedand dried at 55 C and pressure of 10 mmHg. The yield ofAG12-EC, AG10-EC and AG08-EC determined by HPLCwas about 95, 96 and 96 % respectively.
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