生物活性糖苷的合成研究

【作者】 郭瑞霞；

【导师】 方志杰； 李伟；

【作者基本信息】 南京理工大学 ， 应用化学， 2004， 硕士

【摘要】 本论文研究了具有生物活性的糖苷的合成：对位取代苯酚氧糖苷、5-氟尿嘧啶糖苷、腺嘌呤糖苷、黄酮糖苷。 在糖的选择性脱保护中，以氨基葡萄糖盐酸盐为原料，经乙酸酯保护和乙酰基转移两步反应合成了2-乙酰氨基-3，4，6-三-○-乙酰基葡萄糖，该路线是对原有文献的改进和创新。 用三氯乙酰亚胺酸酯法合成了对羟基苯甲酸甲酯葡萄糖苷和对羟基苯乙酮葡萄糖苷。 用直接苷化法，由β-构型的全乙酰化糖合成了5-氟尿嘧啶糖苷和腺嘌呤糖苷。 首次由固—液相转移催化法以溴代四乙酰葡萄糖和7-羟基黄酮为原料以四丁基溴化胺为催化剂合成了葡萄糖、半乳糖、木糖、阿拉伯糖、鼠李糖的7-羟基黄酮苷，其中7-羟基黄酮木糖苷、7-羟基黄酮阿拉伯糖苷和7-羟基黄酮鼠李糖苷是未见文献报道合成过的化合物。 对上述化合物结构进行了质谱、红外、核磁表征。更多还原

【Abstract】 In this thesis, the synthesis of biological glycosides such as p-substituted phenyl- P -D-glucosides, 5-fuorouracil glycosides, adenine glycosides and 7-hydroxyflavone glycosides were studied.In the selective deprotection of sugars, a novel method for the synthesis of 2-acetylamino-3,4,6-tri-O-acetyl-2-deoxy-D-glucose from D-glucosamine hydrochloride via acetyl-protection reaction and acetyl-transformation reaction was discribed. It was an improvement of the method of reference.Two compounds which were O-(4-methoxycarboxyl)phenyl-β-D-glucopyranoside andO-(4-methylketo)phenyl-β-D-glucopyranoside were synthesized through trichloroacetimidate.5-Fuorouracil glycosides and adenine glycosides were prepared via β-peracetylglycose.A series of flavone-7-O-glycosides by reaction of 7-hydroxyflavone and a -D-manose bromide were first synthesized under Bu4NBr as the phase-transfer catalyst.Their structures were identified by MS, IR and NMR.更多还原