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Method for synthesizing dendritic compound trifluoroacetate with cage type octa (gamma-aminopropyl) silsesquioxane as core

A technology of trifluoroacetate and silsesquioxane, which is applied in the field of synthesizing dendrimer trifluoroacetate with cage octapoly(γ-aminopropyl) silsesquioxane as the core

Inactive Publication Date: 2013-03-13
NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has four condensation and four deprotection steps, and each condensation step requires a 3.75-fold excess of HOBt, HBTU, and lysine dicyclohexylamine salt relative to the number of amino groups on the starting material, and these excess compounds can cause Severe environmental pollution; In addition, this method not only has a long reaction time, and each step of reaction needs about two days (48 hours), and a thick paste will be formed when the reaction mixture is added in the aqueous citric acid solution in the aftertreatment step , the paste cannot be filtered, and the water-soluble impurities wrapped in it must be repeatedly diffused and washed for at least 6 times, each time for 5 hours, to be basically removed
This situation results in long post-processing and cumbersome operations
And the overall yield of the reaction is not high, only 4.32%

Method used

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  • Method for synthesizing dendritic compound trifluoroacetate with cage type octa (gamma-aminopropyl) silsesquioxane as core
  • Method for synthesizing dendritic compound trifluoroacetate with cage type octa (gamma-aminopropyl) silsesquioxane as core

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 1. Dissolve OAS hydrochloride (0.50g, 0.43mmol) and DIPEA (0.89g, 6.88mmol) in 20ml DMF, stir for 30min, then add N,N'-di-tert-butoxy in 30ml DMF drop by drop Carbonyl-L-lysine N-succinimide ester (3.05g, 6.88mmol), stirred at room temperature for 12 hours. After the reaction was completed, 150ml of acetonitrile chilled to 0°C was added, filtered, and the resulting solid was vacuum-dried at room temperature for 24 hours to obtain tert-butoxycarbonyl-protected G1(OL) (1.21g, 0.34mmol), with a yield of 80%.

[0028] 2. Add tert-butoxycarbonyl-protected G1(OL) (1.02g, 0.29mmol) into trifluoroacetic acid (5ml) chilled to 0°C and stir for 4 hours. After the reaction was completed, the reaction mixture was added to 50 ml of diethyl ether cooled to 0°C, and the precipitate was collected by filtration to obtain 0.80 g (0.21 mmol) of G1(OL) trifluoroacetate, with a yield of 74%.

[0029] 3. Using G1(OL) trifluoroacetate as raw material, G1(OL) trifluoroacetate, DIPEA and N,N'-d...

Embodiment 2

[0033] 1. Dissolve OAS hydrochloride (0.50g, 0.43mmol) and DIPEA (0.89g, 6.88mmol) in 20ml DMF, stir for 30min, then add N,N'-di-tert-butoxy in 30ml DMF drop by drop Carbonyl-L-lysine pentafluorophenol ester (3.52g, 6.88mmol), stirred and reacted at room temperature for 8 hours. After the reaction was completed, 150ml of acetonitrile chilled to 0°C was added, filtered, and the obtained solid was vacuum-dried to obtain tert-butoxycarbonyl-protected G1(OL) (1.28g, 0.37mmol), with a yield of 85%.

[0034] 2. Add tert-butoxycarbonyl-protected G1(OL) (1.02g, 0.29mmol) into trifluoroacetic acid (5ml) chilled to 0°C and stir for 4 hours. After the reaction was completed, the reaction mixture was added to 50 ml of diethyl ether cooled to 0°C, and the precipitate was collected by filtration to obtain 0.86 g (0.23 mmol) of G1(OL) trifluoroacetate, with a yield of 80%.

[0035] 3. Using G1(OL) trifluoroacetate as raw material, the moles of G1(OL) trifluoroacetate, DIPEA and N,N'-di-tert...

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Abstract

The invention discloses a method for synthesizing a dendritic compound trifluoroacetate with cage type octa (gamma-aminopropyl) silsesquioxane as a core. The method comprises the steps of: dissolving OAS hydrochloride and DIPEA in DMF, dropwise adding DMF N, N '-bis-(tert-butyloxycarbonyl)-L-lysine N-saccinimidyl or N, N'-bis-(tert-butyloxycarbonyl)-L-lysine pentaflurophenyl soluble in DMF, and reacting for 10-14h; adding acetonitrile of -2-2 DEG C, filtering and drying for 20-24 h to obtain t-butyloxycarboryl protected G1 (OL); adding G1 (OL) to trifluoroacetic acid at -2-2 DEG C, and reacting for 3-5h; adding the reaction mixture into diethyl ether of 2-5 DEG C, mixing, standing, filtering and collecting precipitate to obtain G1 (OL) trifluoroacetate; and adjusting reactant proportion, and repeating the above process to obtain the G4 (OL) trifluoroacetate. The invention has advantages of little pollution, short reaction time, simple post-treatment and high yield.

Description

technical field [0001] The invention relates to a method for synthesizing a dendrimer trifluoroacetate (G4(OL) trifluoroacetate) with a cage octamer (γ-aminopropyl) silsesquioxane as the core. Background technique [0002] Organic molecules with a dendritic structure are called dendrimers. Dendrimers generally consist of a core at the center of the molecule and monomers extending outward from the core. Depending on the number of layers of repeating monomers, one generation, two generation up to n generation dendrimers can be formed. like figure 1 As shown, the nucleus (G0) of this dendrimer has three layers of repeated monomers on the periphery, so it is a three-generation dendrimer (G3 for short). [0003] Dendritic compounds are widely used and can be used as catalysts, carriers of drugs or medical contrast agents, etc. Common dendrimers include porphyrin dendrimers, aryl ether dendrimers, polyamide-amine dendrimers (PAMAM), ferrocenyl dendrimers and the like. Cage oc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00
Inventor 骆成才胡桂香沈银周赛春
Owner NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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