AgOTfa/SnCl_4路易斯酸催化的糖苷化反应及微波辅助技术应用
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摘要
糖类是生命体内重要的信息物质,可在微克级甚至纳克级下起作用,在细胞间的相互识别和相互作用、水和电解质的输送、癌细胞的发生和转移、机体的免疫和免疫抑制、以及受精和细胞凝集等生物过程中都起着关键的作用。由于糖类物质对生命科学的重要意义,使以糖为基础研究糖类新药及糖的生物学行为成为生命科学领域中的研究热点,而以化学合成方法获得结构组分专一、高纯度糖活性物质则是上述研究的关键。
本文进行了毗喃糖环C-2位特异性脱保护基合成条件的探索；同时对氧糖苷合成中的端基异构立体选择性进行了研究,探讨了醇类配基对端基异构现象的影响；对微波辅助技术在氧糖苷合成中的应用进行了研究,并利用微波技术,探索了熊果苷及其类似物的绿色化学合成方法。
1.糖类化合物的合成中,在糖环自由羟基上的区域选择性反应有重要的意义。糖类化合物结构设计、天然糖类化合物的合成及糖环中高效药效基团的引入都与此类选择性合成戚戚相关；同时,糖环羟基的区域选择性合成对于寡糖、多糖的设计、合成策略也有重要的作用。糖环中可在多个位置对羟基进行选择性合成,其中具有C-2自由羟基的单糖是非常有用的合成中间体,广泛的应用于生物活性单糖、寡糖、多糖的合成,也能在特定条件下依特殊需要进行构型翻转。糖化学合成中,乙酰基是一个常用的糖环羟基保护基,所以对其选择性脱保护是本文关注的重点。本文应用路易斯酸催化体系,对常用的全乙酰基保护葡萄糖进行了C-2特异性去保护的探素研究,期望寻找到温和、高效的C-2特异性去保护基反应合成条件。在SnCl4和TMSCl的催化下,得到了最高收率为47%的C-2特异性去保护基的产物。与王彦广等方法相比,条件更为温和,在脱保护的同时,也进行了氧苷化反应。同时讨论了不同的路易斯酸催化剂对反应结果的影响,并对C-2去保护基的反应机理进行了阐述。且在前期工作研究的基础上,对C-2位脱氧糖苷的合成,也进行了探索研究。
2.在糖类化合物的合成中,异头碳上C-X(X=C,O,N, S…)糖苷键的构型,无论是对于化合物本身结构的物理、化学、生物稳定性,还是对于其所具有的生物活性,有直接的联系。“端基异构”的一对糖化合物异构体,其所表现出的理化性质、生物活性性质大相径庭。本文对氧糖苷合成过程中端基异构现象进行了研究和讨论,应用AgOTfa/SnCl4和SnCl4两种催化体系,对氧糖苷合成的机理及催化剂对端基氧苷键立体选择性的影响进行研究。通过实验比对,推测了可能的2种反应历程,并推测端基氧苷键立体选择性与参与反应的醇类化合物也有一定的联系。根据Kishi推测的糖类化合物结构中C-2取代基的立体构型对端基异构化的可能反应机理,本文通过对比实验,推测了新的端基异构反应机理。
3.微波辅助技术作为环境友好方法,已被广泛的应用于有机合成中。在糖类化合物的合成中,微波辅助技术也被证明是一种有效的手段。本文对微波辅助技术在氧糖苷合成中的应用进行了尝试,结果表明微波辅助技术能有效地加快糖苷化反应进程。随着全球所面临的生态环境的严峻形势,发展“环境友好”化学合成方法—“绿色化学”成为研究热点：利用化学原理从源头上减少和消除化学工业生产对环境的污染。本文应用微波技术,对已有的熊果苷类似物合成方法进行改善,提高了熊果苷类似物1’-O-4-羟基苯基-2’,3’,4’,6’-四-O-乙酰基-α/β-D-吡喃葡萄糖的收率(比常规化学法提高20%),并大大缩短了反应时间。同时,为了减少反应中废液、废气排放,达到环保目的,本文采用了可回收利用的固体酸催化剂蒙脱石,并通过微波——蒙脱石联用,对熊果苷的绿色合成方法进行了探索实验,为进一步实现熊果苷制备的绿色工艺奠定了基础。
Saccharides play a very important role in life sciences. As known, a variety of biological recognition events such as bacterial and viral infection, cancer metastasis and inflammatory reactions are dependent upon carbohydrates. Up to date, the saccharide study on novel medicines and biotechnology has become one of hot areas, especially developing biological glycoconjugates with activity.
In this dissertation, we studied the-reaction conditions for regioselective deacetylation on the C-2position of glucopyranoside, and propossing the mechanism of anomeric effect on the process of O-glycosidation the configuration at the position of anomeric carbon was proposed when alcohols participated as a ligand. Additionally, the microwave-assisted technology was introduced into O-glycosidation as a green synthesis for arbino and its analogouses.
1. In glycochemistry, the region-and stereo-selctivity for free hydroxyl groups has become a very important issue, which is involed in the structure design of carbohydrates, the synthesis of nature carbohydrate, and the introducing of pharmacophore. Moreover, it's important to the synthesis of oligosaccharides and the configuration inversion of hydroxyl group. Since acetyl group has been widely used as a protecting group for hydroxyl groups in carbohydrate chemisty, we focused on the regioselective deacetylations. We choosed penta-acetate glucose with Lewis acids as a catalyst to successfully realize the regioselective deacetylation of C-2position with the highest yield (47%) under mild condition. the mechanism of C-2deacetyaltion and the effect of diffient Lewis acids were discussed. In addition,2-deoxy sugar based on the former research was synthesized.
2. In carbohydrate chemistry, the configurations of C-X (X=C, O, N, S) bond at the position of anomeric carbon have a great effect on the stabiliby of the physical characteristics, biological nature and activity. Exactly, the two isomers with the only difference in anomeric carbon positon can show completely different properties from physics to biology. In this dissertation, we well discussed anomeric effect on the synthesis of O-glycosation using two catalyst systems (AgOTfa/SnCl4and SnCl4). Two mechanisms are propersed for the kind of reactions and the catalyst system. Interestingly, the alcohol structure plays role in the configuration at the position of anomeric carbon. In contast with the reported mechanism by Kishi. We propose a new explanation for this kind of reaction with similar reaction condition.
3. As a green technology, the microwave-assisted technology was widely used in the organic synthesis. For glycochemisty, it's was also proved to be an effiective condition to distintly shorten the reaction time and increase yield in the synthesis of arbino analogouses has several shortages, such as expensive, too long time, low yield. By using the microwave-assisted technology, we have successfully increased the yield of the analogouses (compound43,44) from17.6%to38.4%. Moreover, we directly synthesized arbino with Montmeonrilonite as a reusable solid acid catalyst by using the microwave-assisted technology.
本文进行了毗喃糖环C-2位特异性脱保护基合成条件的探索；同时对氧糖苷合成中的端基异构立体选择性进行了研究,探讨了醇类配基对端基异构现象的影响；对微波辅助技术在氧糖苷合成中的应用进行了研究,并利用微波技术,探索了熊果苷及其类似物的绿色化学合成方法。
1.糖类化合物的合成中,在糖环自由羟基上的区域选择性反应有重要的意义。糖类化合物结构设计、天然糖类化合物的合成及糖环中高效药效基团的引入都与此类选择性合成戚戚相关；同时,糖环羟基的区域选择性合成对于寡糖、多糖的设计、合成策略也有重要的作用。糖环中可在多个位置对羟基进行选择性合成,其中具有C-2自由羟基的单糖是非常有用的合成中间体,广泛的应用于生物活性单糖、寡糖、多糖的合成,也能在特定条件下依特殊需要进行构型翻转。糖化学合成中,乙酰基是一个常用的糖环羟基保护基,所以对其选择性脱保护是本文关注的重点。本文应用路易斯酸催化体系,对常用的全乙酰基保护葡萄糖进行了C-2特异性去保护的探素研究,期望寻找到温和、高效的C-2特异性去保护基反应合成条件。在SnCl4和TMSCl的催化下,得到了最高收率为47%的C-2特异性去保护基的产物。与王彦广等方法相比,条件更为温和,在脱保护的同时,也进行了氧苷化反应。同时讨论了不同的路易斯酸催化剂对反应结果的影响,并对C-2去保护基的反应机理进行了阐述。且在前期工作研究的基础上,对C-2位脱氧糖苷的合成,也进行了探索研究。
2.在糖类化合物的合成中,异头碳上C-X(X=C,O,N, S…)糖苷键的构型,无论是对于化合物本身结构的物理、化学、生物稳定性,还是对于其所具有的生物活性,有直接的联系。“端基异构”的一对糖化合物异构体,其所表现出的理化性质、生物活性性质大相径庭。本文对氧糖苷合成过程中端基异构现象进行了研究和讨论,应用AgOTfa/SnCl4和SnCl4两种催化体系,对氧糖苷合成的机理及催化剂对端基氧苷键立体选择性的影响进行研究。通过实验比对,推测了可能的2种反应历程,并推测端基氧苷键立体选择性与参与反应的醇类化合物也有一定的联系。根据Kishi推测的糖类化合物结构中C-2取代基的立体构型对端基异构化的可能反应机理,本文通过对比实验,推测了新的端基异构反应机理。
3.微波辅助技术作为环境友好方法,已被广泛的应用于有机合成中。在糖类化合物的合成中,微波辅助技术也被证明是一种有效的手段。本文对微波辅助技术在氧糖苷合成中的应用进行了尝试,结果表明微波辅助技术能有效地加快糖苷化反应进程。随着全球所面临的生态环境的严峻形势,发展“环境友好”化学合成方法—“绿色化学”成为研究热点：利用化学原理从源头上减少和消除化学工业生产对环境的污染。本文应用微波技术,对已有的熊果苷类似物合成方法进行改善,提高了熊果苷类似物1’-O-4-羟基苯基-2’,3’,4’,6’-四-O-乙酰基-α/β-D-吡喃葡萄糖的收率(比常规化学法提高20%),并大大缩短了反应时间。同时,为了减少反应中废液、废气排放,达到环保目的,本文采用了可回收利用的固体酸催化剂蒙脱石,并通过微波——蒙脱石联用,对熊果苷的绿色合成方法进行了探索实验,为进一步实现熊果苷制备的绿色工艺奠定了基础。
Saccharides play a very important role in life sciences. As known, a variety of biological recognition events such as bacterial and viral infection, cancer metastasis and inflammatory reactions are dependent upon carbohydrates. Up to date, the saccharide study on novel medicines and biotechnology has become one of hot areas, especially developing biological glycoconjugates with activity.
In this dissertation, we studied the-reaction conditions for regioselective deacetylation on the C-2position of glucopyranoside, and propossing the mechanism of anomeric effect on the process of O-glycosidation the configuration at the position of anomeric carbon was proposed when alcohols participated as a ligand. Additionally, the microwave-assisted technology was introduced into O-glycosidation as a green synthesis for arbino and its analogouses.
1. In glycochemistry, the region-and stereo-selctivity for free hydroxyl groups has become a very important issue, which is involed in the structure design of carbohydrates, the synthesis of nature carbohydrate, and the introducing of pharmacophore. Moreover, it's important to the synthesis of oligosaccharides and the configuration inversion of hydroxyl group. Since acetyl group has been widely used as a protecting group for hydroxyl groups in carbohydrate chemisty, we focused on the regioselective deacetylations. We choosed penta-acetate glucose with Lewis acids as a catalyst to successfully realize the regioselective deacetylation of C-2position with the highest yield (47%) under mild condition. the mechanism of C-2deacetyaltion and the effect of diffient Lewis acids were discussed. In addition,2-deoxy sugar based on the former research was synthesized.
2. In carbohydrate chemistry, the configurations of C-X (X=C, O, N, S) bond at the position of anomeric carbon have a great effect on the stabiliby of the physical characteristics, biological nature and activity. Exactly, the two isomers with the only difference in anomeric carbon positon can show completely different properties from physics to biology. In this dissertation, we well discussed anomeric effect on the synthesis of O-glycosation using two catalyst systems (AgOTfa/SnCl4and SnCl4). Two mechanisms are propersed for the kind of reactions and the catalyst system. Interestingly, the alcohol structure plays role in the configuration at the position of anomeric carbon. In contast with the reported mechanism by Kishi. We propose a new explanation for this kind of reaction with similar reaction condition.
3. As a green technology, the microwave-assisted technology was widely used in the organic synthesis. For glycochemisty, it's was also proved to be an effiective condition to distintly shorten the reaction time and increase yield in the synthesis of arbino analogouses has several shortages, such as expensive, too long time, low yield. By using the microwave-assisted technology, we have successfully increased the yield of the analogouses (compound43,44) from17.6%to38.4%. Moreover, we directly synthesized arbino with Montmeonrilonite as a reusable solid acid catalyst by using the microwave-assisted technology.
引文
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