半乳糖伯羟基氧化及其衍生物的合成

The Oxidation of Primary Hydroxyl Group of Galactose and the Synthesis of Its Derivatives

以D-半乳糖为起始原料,对其伯羟基进行选择性氧化,由1,2:3,4-二-O-异亚丙基-α-D-吡喃半乳糖(1)得到1,2:3,4-二-O-异亚丙基-α-D-半乳己二醛-1,5-吡喃糖(2),2分别与不同的酰肼、肼反应,得到相应的1,2:3,4-二-O-异亚丙基-α-D-半乳己二醛吡喃糖(杂环基及芳基)取代酰腙(3a^3f)和1,2:3,4-二-O-异亚丙基-α-D-半乳己二醛吡喃糖取代芳基腙(4a^4b)。将化合物1与糖基异硫氰酸酯发生亲核加成反应,合成了一系列6-O-[N-(2,3,4,6-四-O-乙酰基糖基)硫代氨甲酰基]-1,2:3,4-二-O-异亚丙基-α-D-吡喃半乳糖(5a^5e)。化合物的结构经IR1、H NMR、元素分析测试技术进行确定。

By the oxidation of primary hydroxyl group of 1,2 ： 3,4-di-O-isopropylidene-α-D-galactopyranose （1）, 1,2 ： 3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose （2） was prepared. By reaction of compound 2 with hydrazines or hydrazides, a series of 1,2：3,4-di-O-isopropylidene-α-D-galacto-hexodialdo- 1,5-pyranose（ heterocyclyl or aryl） substituted carbonyl hydrazone （3a-3f） and 1,2 ： 3,4-di-O-isopropyli-dene-α-D-galacto-hexodialdo-1,5-pyranose substituted aryl hydrazone（4a,4b） were prepared. By nucleophilic addition reaction of compound 1 with glycosyl isothiocyanates, a series of new compounds 6-O-[N-（ 2,3,4,6- tetra-O-acetyl-glycosyl） thiocarbamoyl ] -1,2 ： 3,4-di-O-isopropylidene-ot-D-galactopyranose （ 5a - 5e ） were prepared. The structures of all the compounds were established by IR, 1H NMR and elemental analysis.