Synthesis of non-ionic amphiphiles from 1,4-anhydroxylitol
a technology of anhydropentitol and amphiphile, which is applied in the preparation of sulfonic acid esters, enzymology, organic chemistry, etc., can solve the problem of relatively limited attention
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example 1
Preparation of 2,5-anhydroarabitol Mono, Di, and Tri Oleates
[0052]Experimental: A flame dried, single neck, 50 mL round bottomed flask equipped with a PTFE coated magnetic stir bar was charged with 1 g of 2,5-anhydroarabitol (7.46 mmol), 3.37 g of oleoyl chloride (11.12 mmol), 5 mL of pyridine, and 20 mL of methylene chloride. The reaction was stirred at room temperature overnight. After this time, excess solvent was removed via rotary evaporation (50° C., 25 torr) and the dark brown residue taken up in a minimum volume of methylene chloride. The mixture was then charged to a pre-fabricated silica gel column, where three separate fractions were collected deploying a methylene chloride / methanol gradient. The first fraction manifested an Rf=0.92 (10:1 hexane / methanol), and furnished a viscous oil after drying. 1H and 13C NMR confirmed the identity as 2,5-anhydroarabitol trioleate. The second fraction manifested an Rf=0.61 (10:1 hexane / methanol), furnishing a pale yellow viscous oil af...
example 2
Synthesis of Triflated 2,5-Anhydroarabitol Monooleates
[0053]Experimental: A flame dried, single neck, 25 mL round bottomed flask equipped with a PTFE coated magnetic stir bar was charged with 500 mg of 2,5-anhydroarabitol monooleates (1.25 mmol), 404 uL of pyridine (5.02 mmol), and 10 mL of anhydrous methylene chloride. The flask stoppered with a rubber septum and then immersed in a saturated brine / ice bath (˜−10° C.). While vigorously stirring, 463 uL of triflic anhydride (2.75 mmol) was added drop wise over a period of 20 min. After addition, the saline bath was removed and reaction continued overnight. The next morning a light yellow solution was observed; excess solvent and pyridine was removed under reduced pressure, and the dark yellow residue taken up in a minimum amount of chloroform, which was then charged to a prefabricated silica gel column that employed a hexanes / ethyl acetate gradient. The triflated title compounds eluted at a 5:1 hexanes / ethyl acetate proportion, furni...
example 3
Synthesis of AEEA-Derivitized 2,5-Anhydroarabitol Monooleates
[0054]Experimental: An oven dried, 25 mL round bottomed flask equipped with a PTFE coated magnetic stir bar was charged with 500 mg of triflated 2,5-anhydroarabitol monooleates (0.754 mmol), 168 uL of 2-((2-aminoethyl)amino)ethanol (AEEA, 1.66 mmol), and 10 mL of absolute ethanol. A reflux condenser was affixed to the neck, and, while vigorously stirring, the mixture was heated to 50° C. overnight. After this time, TLC (neutral alumina, isocratic ethanol eluent) indicated that all of the starting triflate had been consumed, manifesting a single product with an Rf=0.23. The solution was then cooled to room temperature, then poured directly onto a prefabricated Brockmann I activated, neutral alumina column where the AEEA targets were observed to elute using an isocratic ethanol mobile phase. After drying under high vacuum for period of 7 days, 281 mg of the AEEA derivitized monooleates were retained as a light yellow semisol...
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