2,3-环氧丙基2,3,4,6-四-O-乙酰基-β-D-吡喃型葡萄糖苷的合成

Synthesis of 2,3-Epoxypropyl 2, 3, 4, 6-Tetra-O-acetyl-β-D-glucopyranoside

用Fischer Helferich方法,对2,3 环氧丙基2,3,4,6 四 O 乙酰基 β D 吡喃型葡萄糖苷的合成方法进行了研究。以D 葡萄糖为原料,在碱性条件下乙酰化得到1,2,3,4,6 五 O 乙酰基 β D 葡萄糖。然后在SnCl4催化下与烯丙醇反应得到2,3,4,6 四 O 乙酰基 β D 吡喃型葡萄糖烯丙苷。再经间氯过氧苯甲酸氧化得到目标化合物2,3 环氧丙基2,3,4,6 四 O 乙酰基 β D 吡喃型葡萄糖苷。其路线要比文献报道的少一步,总收率可达40%。目标化合物的结构经IR、13CNMR、EIMS和元素分析得到了确证。

The synthesis of 2,3-epoxypropyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside through the Fischer-Helferich method was described.2-Propenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside was synthesized by treating peracetylated β-D-glucopyranoside,which was prepared from D-glucose in acetic anhydride-KOAc,with 2-propenyl alcohol and SnCl_4.Epoxidation of 2-propenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside by reacting with m-chloroperbenzoic acid gave 2,3-epoxypropyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in an overall yield of 40%.The structure of target compound was confirmed by IR,^(13)CNMR,EIMS and elementary analysis.