D-甘露庚酮糖的合成及若干庚糖骨架鏈的合成研究
發(fā)布時間：2018-08-07 12:11
【摘要】：庚糖為稀有高碳糖,廣泛分布于高等植物、藻類、真菌和細(xì)菌當(dāng)中,具有多種生物活性。D-甘露庚酮糖為天然庚酮糖,首次分離于鱷梨組織中,通過抑制葡萄糖激酶活性,抑制葡萄糖代謝和胰島素分泌,具有提高血糖濃度的作用,能夠作為治療低血糖癥的潛在藥物,其合成研究具有重要意義。目前已有的關(guān)于庚糖,尤其是D-甘露庚酮糖的合成,主要依賴于重排反應(yīng)和以"6+1"、"5+2"為主的碳鏈延伸反應(yīng)。本文開發(fā)了一種"4+3"碳鏈延伸方法,合成了 D-甘露庚酮糖。首先以D-來蘇糖為原料,經(jīng)過一系列官能團轉(zhuǎn)化得到四碳醛砌塊。然后通過對L-proline催化的aldol/hemiketalization串聯(lián)反應(yīng)的優(yōu)化,構(gòu)建了不同保護基保護的庚酮糖砌塊。最后經(jīng)保護基脫除工作得到D-甘露庚酮糖。論文提出的新型合成策略為不同構(gòu)型的庚酮糖的合成提供了借鑒。
[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.
【學(xué)位授予單位】：華東理工大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：R914.5
本文編號：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.
【學(xué)位授予單位】：華東理工大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：R914.5
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