Synthesis method of mono-sulfhydryl bis-hexadecyl ether polyethylene glycol interchain oligosaccharide glycolipid
A technology of monomercapto dihexadecyl ether and triphenylthio dihexadecyl ether, which is applied in the field of chemical synthesis and can solve the problem of difficulty in obtaining amphiphilic aliphatic chain polyethylene glycol interchain glycolipids containing mercapto groups, etc. problem, to achieve the effect of low breakthrough yield, high product yield, simple and efficient method
Active Publication Date: 2019-10-22
JIANGSU INST OF METROLOGY
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Problems solved by technology
[0005] The purpose of the present invention is to solve the synthetic problem of amphiphilic mercapto-polyethylene glycol interchain oligosaccharide glycolipid, and provide a kind of synthetic method of monomercapto dihexadecyl ether polyethylene glycol interchain oligosaccharide glycolipid, Solving the problem that amphiphilic glycolipids containing thiol-containing fatty chains and polyethylene glycol interchain chains is not easy to obtain is of great significance for the study of specific recognition and targeted drug delivery of glycolipids on the surface of tumor cells
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Embodiment 1
[0063] (1) Synthesis of Allyloxytriethylene Glycol (TG-Ally)
[0064] Dissolve 10 mL of triethylene glycol in 30 mL of dry THF, stir at room temperature for 30 min, add 3.5 g of pure sodium and stir rapidly for 1 h, add dropwise 15 mL of allyl bromide, and continue the reaction for 6 h. The residue after vacuum distillation was dissolved in 30 mL of dichloromethane, washed with saturated NaCl solution, dried over anhydrous magnesium sulfate, filtered and concentrated, and purified by column chromatography to obtain 4 g of a colorless oily product with a yield of 80%.
[0065] Column chromatography: Silica gel: Et 2 O / EtOAc 1:1
[0066] (2) Synthesis of allyloxytriglycol acyl mannose
[0067] 0.5g 2,3,4,6-O-acetyl-α-D-mannopyranose trichloroacetimidate and 1.25g TG-Allyl were mixed and dissolved in 10mL dry THF, stirred at room temperature for 30min, quickly Add 125 μL TMSOTf dropwise, after stirring continuously for 30 h, add 125 μL ethanolamine to decompose excess TMSOT, w...
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The invention discloses a synthesis method of mono-sulfhydryl bis-hexadecyl ether polyethylene glycol interchain oligosaccharide glycolipid. The method is characterized in that 2,3,4,6-O-acetyl-alpha-D-mannopyranose trichloroacetimidate and allyloxy triethylene glycol are used for synthesizing epoxypropyl triethylene glycol acyl mannose in the serial reaction in which chloroperoxybenzoic acid MCPBA and trimethylsilyl trifluoromethanesulfonate TMSOTf are adopted as catalysts; the mannose derivative is sequentially mixed with cetyl alcohol and triphenyl heptadecyl methanesulfonate, and triphenyl-dihexadecyl polyethylene glycol mannose is synthesized by taking sodium hydride as a strong base and adopting boron trifluoride diethyl ether BF3-C2H6O and tetrabutylammonium iodide TABI as catalysts; finally, triphenyl-dihexadecyl polyethylene glycol mannose is mixed with trifluoroacetic acid TFA under the condition of sodium superbase blocks and subjected to a reaction under the catalysis of aphase transfer catalyst benzyl triethyl ammonium chloride TEBA to obtain a target product, namely the mono-sulfhydryl bis-hexadecyl ether polyethylene glycol interchain oligosaccharide glycolipid. Themethod fills up the blank of the synthesis of amphiphilic oligosaccharide containing sulfhydryl difatty chains in the prior art.
Description
technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of monomercapto dihexadecyl ether polyethylene glycol oligosaccharide glycolipid. Background technique [0002] In nature, sugar compounds are often combined with different types of non-sugar natural products in the form of covalent bonds. The sugar moiety plays a role in the storage and transport of biological information in the molecule, and at the same time affects the solubility and selection of molecules. sex and biological activity. The most important class is glycolipid compounds formed by linking sugars and lipids. Sugars in this class of compounds can be used as protein antigens or receptors, reflecting the important biological activities of carbohydrate compounds, while glycolipid compounds loaded on proteins play the role of communication molecules within and between molecules, especially in It plays an important role in biological pro...
Claims
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IPC IPC(8): C07H1/00C07H15/08
CPCC07H1/00C07H15/08
Inventor 郑海富毛朔南马宇明蔡冶强姚成杨梅毛玲妙邢金京王以堃宋栋梁孙磊
Owner JIANGSU INST OF METROLOGY
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