全保护的半乳吡喃糖基(α1→4)-(半乳吡喃糖基)(β1→3)-2-脱氧-2-乙酰氨基-葡萄吡喃糖对甲氧基苯酚苷的合成

目的 合成全保护的半乳吡喃糖基(α1→4)-(半乳吡喃糖基)(β1→3)-2-脱氧-2-乙酰氨基-葡萄吡喃糖对甲氧基苯酚苷。方法 以D-半乳糖和D-氨基葡萄糖盐酸盐为起始原料,采用硫苷和Schmidt苷糖基化高立体选择性、高效地合成2,3,4,6-四-O-苄基-β-D-半乳糖基(α1→4)-(2,3,4,6-四-O-乙酰基-β-D-半乳吡喃糖基)(β1→3)-2-脱氧-2-乙酰氨基-β-D-葡萄糖对甲氧基苯酚苷 (1) 。结果 简便高效地获得了目标化合物,主要反应中间产物以及目标化合物均由1HMNR、13CMNR和质谱确证。结论 选用的保护基合成简单,易脱去,通用性强;糖基化反应立体选择性好,产率高,适用于各种寡糖化合物的合成。
Objective To synthesize fully protected p-methoxyphenyl D-galactopyranosyl(α1→4)-(D-galactopyranosyl)-(β1→3)-2-deoxy-2-acetamido-D-glucopyranoside. Methods With D-galactose and D-glucosamine hydrochloride used as the initial compounds, we stereoselectively and efficiently synthesized p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl (α1→4)-(2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)-(β1→3)-6-benzyl-2-deoxy-2-acetamido-β-D-glucopyranoside (1) by glucosinolates glycosylation and Schmidt glycosylation. Results Our method efficiently produced the target compound, and the structures of the main intermediates and target compound were confirmed by 1HMNR, 13CMNR and MS. Conclusion We have established a simple synthesis method with high universal property for target compound; additionally, the protective base is easily removable. Our method is applicable for the synthesis of various oligosaccharides