N,N′-二茂铁二甲酰氨基葡萄糖的合成

Synthesis of N,N′-Ferrocenedicarbonylgluosamine

报道了以具有抗癌和抗艾滋病毒活性的β-D-氨基葡萄糖与二茂铁二甲酸作起始原料合成一种糖/金属有机化合物--N,N＇-二茂铁二甲酰氨基葡萄糖的方法.第一步,将氨基葡萄糖用苯甲醛保护氨基后,用乙酸酐再保护羟基,然后在加有盐酸的丙酮中去氨基保护,得1,3,4,6-四-O-乙酰基-β-D-氨基葡萄糖盐酸盐;将二茂铁二甲酸与草酰氯在干燥的二氯甲烷中反应得到二茂铁二甲酰氯.第二步,将第一步所得的两个中间产物,在室温下加入干燥的二氯甲烷和苯的混合溶剂中,在三乙胺存在下进行反应,得目标产物,收率35.7%,系红棕色固体,熔点198～200 ℃.目标化合物是具有双药效基团的物质.用元素分析,红外光谱和核磁共振波谱进行了表征.

A compound of metal/sugar N, N＇- （ 1,1 ＇-ferrocenedicarbonyl ） -bis （ 1,3,4,6-tetra-O-acetyl- 2-deoxy-β-D-glucosamine） （ Ⅰ ） was synthesized by the reaction of 1,3,4,6-tetra-O-acetyl-2-deoxy-β- D-glucosamine hydrochloride （ Ⅱ ） and 1, 1＇-ferrocenedicarbonyl chloride （ Ⅲ ）. To obtain Ⅱ, benzaldehyde was used to protect the amino group in glucosamine hydrochloride and acetic anhydride was used to acetylate the hydroxyl groups, then the amino group was deprotected in hydrochloric acid acetone solution. Ⅲ was prepared through the reaction between 1,1 ＇-ferrocenedicarboxylic acid and oxalyl dichloride in dry dichloromethane. Then, at room temperature, the target product I was obtained in 35.7% yield by coupling reaction of Ⅱ and Ⅲ in mixed solvent of dry dichloromethane and benzene in the presence of triethylamine. The product was reddish brown, mp 198 - 200 ℃, and characterized by IR, 1^ HNMR spectra and elementary analysis. It is a drug of dual functions.