含D-氨基葡萄糖分子的酰基硫脲衍生物合成

Syntheses of D-Glucosamine Acylthiourea Derivatives

以D-氨基葡萄糖盐酸盐为原料,经酰化保护羟基后得1,3,4,6-四-O-乙酰基-2-脱氧-β-D-氨基葡萄糖,再与芳酰基异硫氰酸酯反应,合成了12种新型的糖基酰基硫脲衍生物。实验表明,优化反应条件为芳酰异硫氰酸酯∶上述氨基葡萄糖=1∶1.2(摩尔比),在二氯甲烷溶液中加热至40℃,反应6 h。产物结构经IR、~1H NMR、^(13)C NMR分析确证。

Twelve kinds of D-glucosamine acylthiourea derivatives were synthesized from acyl isothiocyanate and1,3,4,6- tetra-O-acetyl-2-deoxy-β-D-glucosamine hydrochloride prepared from D-glucosamine hydrochloride by protection of amino group followed by acetylation of hydroxyl group,and deprotection of the amino group. The optimal conditions for the coupling reaction were the molar ratio of acyl isothiocyanate and 1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucosamine 1∶ 1.2 in dichloromethane at 40℃ for 6 hours. The products were characterized by IR,1H NMR and 13 C NMR.