D-甘露庚酮糖的合成及若干庚糖骨架链的合成研究
发布时间：2018-08-07 12:11
【摘要】：庚糖为稀有高碳糖,广泛分布于高等植物、藻类、真菌和细菌当中,具有多种生物活性。D-甘露庚酮糖为天然庚酮糖,首次分离于鳄梨组织中,通过抑制葡萄糖激酶活性,抑制葡萄糖代谢和胰岛素分泌,具有提高血糖浓度的作用,能够作为治疗低血糖症的潜在药物,其合成研究具有重要意义。目前已有的关于庚糖,尤其是D-甘露庚酮糖的合成,主要依赖于重排反应和以"6+1"、"5+2"为主的碳链延伸反应。本文开发了一种"4+3"碳链延伸方法,合成了 D-甘露庚酮糖。首先以D-来苏糖为原料,经过一系列官能团转化得到四碳醛砌块。然后通过对L-proline催化的aldol/hemiketalization串联反应的优化,构建了不同保护基保护的庚酮糖砌块。最后经保护基脱除工作得到D-甘露庚酮糖。论文提出的新型合成策略为不同构型的庚酮糖的合成提供了借鉴。
[Abstract]:Heptose, a rare and high carbohydrate, is widely distributed in higher plants, algae, fungi and bacteria. It has a variety of biological activities. D- mannoheptose is a natural heptose. It was first isolated from avocado tissue by inhibiting the activity of glucokinase. Inhibition of glucose metabolism and insulin secretion has the effect of increasing blood glucose concentration and can be used as a potential drug for the treatment of hypoglycemia. At present, the synthesis of heptose, especially D-mannoheptose, mainly depends on the rearrangement reaction and the carbon chain extension reaction of "61" and "52". In this paper, a "43" carbon chain extension method was developed to synthesize D-mannoheptanone sugar. At first, D-lethose was used as raw material, and a series of functional groups were transformed to produce four-carbon aldehyde block. Then, by optimizing the aldol/hemiketalization series reaction catalyzed by L-proline, the heptanone sugar block with different protection groups was constructed. Finally, D-mannoheptanone sugar was obtained by removing the protective group. The new synthesis strategy proposed in this paper provides a reference for the synthesis of heptanone sugar with different configurations.
【学位授予单位】：华东理工大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：R914.5
本文编号：2169987
[Abstract]:Heptose, a rare and high carbohydrate, is widely distributed in higher plants, algae, fungi and bacteria. It has a variety of biological activities. D- mannoheptose is a natural heptose. It was first isolated from avocado tissue by inhibiting the activity of glucokinase. Inhibition of glucose metabolism and insulin secretion has the effect of increasing blood glucose concentration and can be used as a potential drug for the treatment of hypoglycemia. At present, the synthesis of heptose, especially D-mannoheptose, mainly depends on the rearrangement reaction and the carbon chain extension reaction of "61" and "52". In this paper, a "43" carbon chain extension method was developed to synthesize D-mannoheptanone sugar. At first, D-lethose was used as raw material, and a series of functional groups were transformed to produce four-carbon aldehyde block. Then, by optimizing the aldol/hemiketalization series reaction catalyzed by L-proline, the heptanone sugar block with different protection groups was constructed. Finally, D-mannoheptanone sugar was obtained by removing the protective group. The new synthesis strategy proposed in this paper provides a reference for the synthesis of heptanone sugar with different configurations.
【学位授予单位】：华东理工大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：R914.5
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