Method for preparing phosphorylated serine phosphonate mimetics
A technology of serine phosphonic acid and simulants, which is applied to the preparation method of peptides, chemical instruments and methods, and compounds of group 5/15 elements of the periodic table, can solve the problems that phosphate simulants need to be improved, and achieve the steps of the reaction route The effect of less, cheap raw materials, and high yield
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Embodiment 1
[0049] Synthesis of N-tert-butoxycarbonyl-homoserine tert-butyl ester (Boc-HoSer-OtBu, compound 2)
[0050]
[0051] Add 2.89g N-tert-butoxycarbonyl-aspartic acid tert-butyl ester (Boc-Asp-OtBu, compound 1) and 1.29g N-hydroxysuccinimide in 100mL round bottom flask, add 50mL ethyl acetate to make It was dissolved, and then 2.26 g of dicyclohexylcarbodiimide was added under stirring, and the stirring reaction was continued overnight at room temperature. Remove insoluble matter by filtration and spin out ethyl acetate on a rotary evaporator, dissolve the residue in 50mL 1,4-dioxane with stirring and add 0.76g sodium borohydride, and cool the mixture to 0°C on an ice bath 3 mL of water was slowly added dropwise, and then the ice bath was removed to continue the reaction at room temperature for 2 hours. Add 10 mL of saturated ammonium chloride solution and stir for 10 minutes. After removing the dioxane on a rotary evaporator, extract the remaining water phase with 100 mL of e...
Embodiment 2
[0053] Synthesis of 2-(tert-butoxycarbonylamino)-4-bromobutanoic acid tert-butyl ester (Boc-Abu(Br)-OtBu, compound 3)
[0054]
[0055] In a 50 mL round bottom flask, add 1.95 g of N-tert-butoxycarbonyl-homoserine tert-butyl ester (Boc-HoSer-OtBu, compound 2) and 1.60 g of N-bromosuccinimide, add 15 mL of anhydrous dichloromethane Mix evenly, cool to 0°C on an ice bath, and slowly add a solution of 2.38g triphenylphosphine dissolved in 10mL anhydrous dichloromethane dropwise with a constant pressure dropping funnel under stirring, and the addition is completed in about 20 minutes; then remove the ice bath and continue to react at room temperature for 2 hours. After the reaction, add 10 mL of water, separate the organic phase, and extract the remaining water phase with 75 mL of dichloromethane three times; combine the organic phase and the extract, wash twice with 20 mL of water and 20 mL of saturated brine, and dry over anhydrous magnesium sulfate , was spin-dried on a rot...
Embodiment 3
[0057] 2-(tert-butoxycarbonylamino)-4-(dibenzylphosphono)butanoic acid tert-butyl ester (Boc-Pma(Bn) 2 -OtBu) synthesis
[0058]
[0059] Add 1.69g 2-(tert-butoxycarbonylamino)-4-bromobutanoic acid tert-butyl ester (Boc-Abu(Br)-OtBu, compound 3) into a 100mL three-necked flask, exchange with argon several times to remove Air in the bottle, then add 1.50g of dibenzyl phosphite dissolved in 10mL of anhydrous acetonitrile, stir and mix evenly. The reaction system was cooled to 0°C on an ice bath, and 1 mL of DBU was slowly added dropwise into the bottle with a syringe. After the addition, the ice bath was removed, and the reaction was continued at room temperature for 8 hours. After the reaction, the acetonitrile solution of the mixture was washed 3 times with 10mL cyclohexane, spin-dried on a rotary evaporator, and then carried out column chromatography with 1:2 ethyl acetate / cyclohexane as a developing solvent to obtain 1.68g 2- (tert-butoxycarbonylamino)-4-(dibenzylphosp...
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