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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1 HMNR、13 CMNR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 galactopyranosyl (α1 → 4) - (galactopyranosyl) (β1 → 3) -2-deoxy-2-acetamido-glucopyranosyl p-methoxyphenolate . Methods D-galactose and D-glucosamine hydrochloride were used as starting materials to synthesize 2,3,4,6-tetra-O-benzyl with high stereoselectivity and glycosylation of glucosinolate and Schmidt glycoside -β-D-galactosyl (α1 → 4) - (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) (β1 → 3) -2-acetylamino-β-D-glucose p-methoxyphenolate (1). Results The target compounds were obtained easily and efficiently. The main reaction intermediates and target compounds were confirmed by 1 HMNR, 13 CMNR and mass spectrometry. Conclusions The protective group is simple, easy to be removed and versatile. The glycosylation reaction has good stereoselectivity and high yield and is suitable for the synthesis of various oligosaccharide compounds.