3-叠氮基丙基-β-D-吡喃半乳糖苷的合成工艺改进

Prrocess Improvement on the Synthesis of 3-Azidopropyl-β-D-galactopyranoside

以D-半乳糖为原料,经苯甲酰化制得1,2,3,4,6-五-氧-苯甲酰基-β-D-吡喃半乳糖苷(2);2与3-氯丙醇在三氟化硼乙醚作用下进行糖苷化反应制得3-氯丙基-2,3,4,6-四-氧-苯甲酰基-β-D-吡喃半乳糖苷(3);3与叠氮钠反应制得3-叠氮基丙基-2,3,4,6-四-氧-苯甲酰基-β-D-吡喃半乳糖苷(4);4在甲醇钠作用下脱苯甲酰基合成了3-叠氮基丙基-β-D-吡喃半乳糖苷,总收率67.8%,其结构经1H NMR和ESI-HR-MS确证。

1,2,3,4,6-Penta-O-benzoyl-β-D-galactopyranoside（2） was prepared by the reaction of Dgalactose with benzoyl chloride. 3-Chloropropyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside （ 3 ） was obtained by glycosidation of 3-chloro propanol with 2 using BF3 · Et2O as catalyst. 3-Azidopropyl β-D-galaetopyranoside in total yield of 67.8% was synthesized by azidation of 3 with sodium azide then removed benzoyl groups with sodium methoxide. The structure was confirmed by 1H NMR and ESI-HR-MS.