β-D-吡喃葡萄糖基咪唑环乙内酰硫脲类化合物合成
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摘要
糖基异硫氰酸酯之所以作为一类特殊的糖类化合物,是因为不仅具有良好的生理功能,而且还是有机合成的重要中间体之一。与烷基或芳香族异硫氰酸酯相似,可发生环加成及亲核加成等反应,而且已经被广泛的用于合成具有潜在药效和生理活性的胍基糖苷、糖基硫脲、糖基杂环化合物,以及糖基氨基酸、糖蛋白质和糖基多肽等糖类衍生物。我们的工作目的是将糖基异硫氰酸酯与修饰的氨基酸结合,形成一类新的硫脲,充分发挥两类分子的活性特点,使之共同起到生物活性的作用。
论文研究了糖基异硫氰酸酯的合成,并进一步合成糖基异硫氰酸酯的咪唑环乙内酰硫脲类化合物。用易得的葡萄糖为原料,经过以下两步反应合成了中间体全乙酰化保护的葡萄糖基异硫氰酸酯首先葡萄糖的乙酰化,其次对其进行端基异硫氰酸化。然后用全酰化的葡萄糖基异硫氰酸酯与甘氨酸甲酯盐酸盐、丙氨酸甲酯盐酸盐、缬氨酸甲酯盐酸盐、苯丙氨酸甲酯盐酸盐、亮氨酸甲酯盐酸盐、异亮氨酸甲酯盐酸盐、蛋氨酸甲酯盐酸盐、半胱氨酸甲酯盐酸盐等八种氨基酸甲酯类进行亲核加成得到糖基咪唑环乙内酰硫脲类化合物,共合成出18个化合物,其中8个葡萄糖基异硫氰酸酯的咪唑环乙内酰硫脲类化合物4a~4h,未见文献报道。通过这些化合物的红外光谱(IR)、核磁共振的氢谱(1HNMR)和高分辨的质谱(ESI-MS)对其进行结构确认和表征,并对其进行了熔点测定,目前正在进行部分目标化合物的生理活性测试。
实验过程中的创新主要有以下几点:
第一、在葡萄糖糖基异硫氰酸酯合成中,参考文献合成方法,但在其后处理过程中进行创新。传统的产物分离使用柱层析的方法进行处理,本实验在产物分离过程中则采用多次重结晶的方法。不仅过程简单,而且产率提高了8﹪,同时还避免了柱层析方法分离过程的繁琐和溶剂的浪费。
第二、脂肪族异硫氰酸酯及芳香族异硫氰酸酯类与氨基酸甲酯的成环反应已有研究,但糖基异硫氰酸酯与其反应的报道鲜为少见。本实验的创新点在于研究氨基酸酯与葡萄糖糖基异硫氰酸酯成环的情况。
第三、葡萄糖糖基异硫氰酸酯与多种反应物在不同的条件下形成多种杂环的反应为参考,研究葡萄糖糖基异硫氰酸酯与氨基酸酯的成环反应。
第四、尝试不同的溶剂体系及反应温度等反应条件合成2,3,4,6-四-O-酰基-β-D-吡喃葡萄糖异硫氰酸酯的咪唑环乙内酰硫脲类化合物,寻找最优化的反应体系。
Glycosyl isothiocyanates as a kind of special carbohydrates,not only has good physiological function, but also is an important intermediate of organic synthesis. And alkyl or aromatic isothiocyanates, as can occur nucleophilic addition and cycloaddition reactions etc. They have been widely used for synthesis of biological activity and potential efficacy of guanidine glycosides, glycosyl thioureas, glycosyl heterocyclic compounds, as well as sugar derivatives of glycosyl amino acids, sugar-protein and protein peptide so on . The purpose of our work is to glycosyl isothiocyanate with the modified amino acids, forming a new class of thiourea, giving full the activity of two types of molecular characteristics, so that together playing a role in biological activity and would be likely to receive a new class of polysaccharide drug.
This essay is mainly studied in synthesis of glycosyl isothiocyanates and further synthesis of pyranoid thiohydantoins. The glucose which is easy to obtain as raw material, the intermediate of the all acylation glucoyranosyl isothiocyanate was synthesized through two steps reaction of whole acylation and end group isothiocyanate. And then make the all acylation glucopyranosyl isothiocyanate and the glycine methyl ester muriate, the alanin methyl ester muriate, the amino-isovaleric acid methyl ester muriate, the phenylalanine methyl ester muriate, the leucine methyl ester muriate, the isoleucine methyl ester muriate, the methionine methyl ester muriate, the cysteine methyl ester muriate and so on eight kind of amino acid methyl ester class carry on the nucleophilic addition to obtain in the sugar base volute second grade the acid radical thiourea class compound. Results, a total of 18 target compounds were synthesized through the experiment. Among of them, eight pyranoid thiohydantoin compounds of 4a ~ 4h have not been reported in the literature. These compounds were characterized by infrared spectrum (IR), nuclear magnetic resonance spectra of hydrogen (1HNMR) and high-resolution mass spectrometry (ESI-MS) identification and characterization of the structure and conduct of the melting point, part of the target compounds physiological activity test is under way. Paper not only draws on the classic separation of the method of synthesis and integration of the innovations to be explored by many experiments in the process of innovation are
mainly the following points:
First, In the glycosyl isothiocyanate synthesis, different from the traditional method of separation of process improvement and product separation method, the direct use of multiple re-crystallization process is simple not only improve the yield, but also avoids the separation of column chromatography the process cumbersome and solvent waste.
Second, Aliphatic and aromatic amino acid methyl ester with the cyclic reaction has been studied, but their response to sugar-based reports for the rare few. Therefore, amino acid ester of sugar and glucose into the ring isothiocyanate situation and amino acid esters of aliphatic and aromatic isothiocyanates were compared.
Thirdly, the glycosyl isothiocyanate reactants with a variety of different conditions in the formation of a variety of heterocyclic reaction as a reference, study and amino acid ester cyclization.
Fourth,try to the different resolver system synthesis of 2,3,4,6-Tetra-O-acetyl-β-D-Gluco pyranoid thiohydantoins and to find the most optimal reaction system.
论文研究了糖基异硫氰酸酯的合成,并进一步合成糖基异硫氰酸酯的咪唑环乙内酰硫脲类化合物。用易得的葡萄糖为原料,经过以下两步反应合成了中间体全乙酰化保护的葡萄糖基异硫氰酸酯首先葡萄糖的乙酰化,其次对其进行端基异硫氰酸化。然后用全酰化的葡萄糖基异硫氰酸酯与甘氨酸甲酯盐酸盐、丙氨酸甲酯盐酸盐、缬氨酸甲酯盐酸盐、苯丙氨酸甲酯盐酸盐、亮氨酸甲酯盐酸盐、异亮氨酸甲酯盐酸盐、蛋氨酸甲酯盐酸盐、半胱氨酸甲酯盐酸盐等八种氨基酸甲酯类进行亲核加成得到糖基咪唑环乙内酰硫脲类化合物,共合成出18个化合物,其中8个葡萄糖基异硫氰酸酯的咪唑环乙内酰硫脲类化合物4a~4h,未见文献报道。通过这些化合物的红外光谱(IR)、核磁共振的氢谱(1HNMR)和高分辨的质谱(ESI-MS)对其进行结构确认和表征,并对其进行了熔点测定,目前正在进行部分目标化合物的生理活性测试。
实验过程中的创新主要有以下几点:
第一、在葡萄糖糖基异硫氰酸酯合成中,参考文献合成方法,但在其后处理过程中进行创新。传统的产物分离使用柱层析的方法进行处理,本实验在产物分离过程中则采用多次重结晶的方法。不仅过程简单,而且产率提高了8﹪,同时还避免了柱层析方法分离过程的繁琐和溶剂的浪费。
第二、脂肪族异硫氰酸酯及芳香族异硫氰酸酯类与氨基酸甲酯的成环反应已有研究,但糖基异硫氰酸酯与其反应的报道鲜为少见。本实验的创新点在于研究氨基酸酯与葡萄糖糖基异硫氰酸酯成环的情况。
第三、葡萄糖糖基异硫氰酸酯与多种反应物在不同的条件下形成多种杂环的反应为参考,研究葡萄糖糖基异硫氰酸酯与氨基酸酯的成环反应。
第四、尝试不同的溶剂体系及反应温度等反应条件合成2,3,4,6-四-O-酰基-β-D-吡喃葡萄糖异硫氰酸酯的咪唑环乙内酰硫脲类化合物,寻找最优化的反应体系。
Glycosyl isothiocyanates as a kind of special carbohydrates,not only has good physiological function, but also is an important intermediate of organic synthesis. And alkyl or aromatic isothiocyanates, as can occur nucleophilic addition and cycloaddition reactions etc. They have been widely used for synthesis of biological activity and potential efficacy of guanidine glycosides, glycosyl thioureas, glycosyl heterocyclic compounds, as well as sugar derivatives of glycosyl amino acids, sugar-protein and protein peptide so on . The purpose of our work is to glycosyl isothiocyanate with the modified amino acids, forming a new class of thiourea, giving full the activity of two types of molecular characteristics, so that together playing a role in biological activity and would be likely to receive a new class of polysaccharide drug.
This essay is mainly studied in synthesis of glycosyl isothiocyanates and further synthesis of pyranoid thiohydantoins. The glucose which is easy to obtain as raw material, the intermediate of the all acylation glucoyranosyl isothiocyanate was synthesized through two steps reaction of whole acylation and end group isothiocyanate. And then make the all acylation glucopyranosyl isothiocyanate and the glycine methyl ester muriate, the alanin methyl ester muriate, the amino-isovaleric acid methyl ester muriate, the phenylalanine methyl ester muriate, the leucine methyl ester muriate, the isoleucine methyl ester muriate, the methionine methyl ester muriate, the cysteine methyl ester muriate and so on eight kind of amino acid methyl ester class carry on the nucleophilic addition to obtain in the sugar base volute second grade the acid radical thiourea class compound. Results, a total of 18 target compounds were synthesized through the experiment. Among of them, eight pyranoid thiohydantoin compounds of 4a ~ 4h have not been reported in the literature. These compounds were characterized by infrared spectrum (IR), nuclear magnetic resonance spectra of hydrogen (1HNMR) and high-resolution mass spectrometry (ESI-MS) identification and characterization of the structure and conduct of the melting point, part of the target compounds physiological activity test is under way. Paper not only draws on the classic separation of the method of synthesis and integration of the innovations to be explored by many experiments in the process of innovation are
mainly the following points:
First, In the glycosyl isothiocyanate synthesis, different from the traditional method of separation of process improvement and product separation method, the direct use of multiple re-crystallization process is simple not only improve the yield, but also avoids the separation of column chromatography the process cumbersome and solvent waste.
Second, Aliphatic and aromatic amino acid methyl ester with the cyclic reaction has been studied, but their response to sugar-based reports for the rare few. Therefore, amino acid ester of sugar and glucose into the ring isothiocyanate situation and amino acid esters of aliphatic and aromatic isothiocyanates were compared.
Thirdly, the glycosyl isothiocyanate reactants with a variety of different conditions in the formation of a variety of heterocyclic reaction as a reference, study and amino acid ester cyclization.
Fourth,try to the different resolver system synthesis of 2,3,4,6-Tetra-O-acetyl-β-D-Gluco pyranoid thiohydantoins and to find the most optimal reaction system.
引文
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