2-脱氧-1,6-二-O-乙酰基-3,4-二-O-苄基-2-叠氮基-α-D-吡喃葡萄糖的合成

Synthesis of 1,6-Di-O-acetyl-2-azido-3,4-di-benzyl-2-deoxy-α-D-glucopyranose

以N-乙酰氨基葡萄糖为起始原料,依次通过甲苷化、叠氮化、苄基保护和乙酰酯交换4步反应得到构型单一的磺达肝癸钠中间体,即标题化合物,总收率为46.2%。目标产物结构通过IR、ESI-MS、1HNMR和13CNMR鉴定,纯度通过HPLC分析。该合成方法具有路线简短、原料和试剂价廉易得、安全性高且化合物构型易控制等优点,可为投入工业化生产提供方法参考。

Starting from N-acetyl-D-glucosamine,intermediate compound for fondaparinux sodium was obtained in four steps including glycoside,azide,benzyl protection and acetyl ester-exchange. The total yield was 46. 2%. The structure of the target compound was confirmed by IR,ESI-MS,1HNMR and13 CNMR,and its purity was analysized by HPLC. This preparative method is simple,and the raw materials and reagents were cheap and safety. The configuration of the compound was easy to control. All these showed it might provide a methodological reference for industrial production.