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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

Synthesis of protected p-methoxyphenyl D-galactopyranosyl(α1→4)-(D-galactopyranosyl)-(β1→3)-2-deoxy-2-acetamido-D-glucopyranoside
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摘要 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 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 stereoseleetively and efficiently synthesized p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl （α1→ 4 ）-（ 2, 3, 4, 6-tetra-O-benzyl-D-galaetopyranosyl）-（β1→3 ）-6-benzyl-2-deoxy-2-acetamido-fl-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.
作者 黄蕾 李翔 胡宏岗 俞世冲 吴秋业
机构地区 第二军医大学药学院有机化学教研室
出处 《第二军医大学学报》 CAS CSCD 北大核心 2016年第2期145-152,共8页 Academic Journal of Second Military Medical University
基金 国家科技重大专项(2012ZX09502001-005 2011ZXJ09201-012) 国家自然科学基金青年项目(21202200)~~
关键词 糖基化 三糖类 炭疽芽孢杆菌 化学合成 glyeosylation trisaccharides Bacillus anthracis chemosynthesis
分类号 R378.72 [医药卫生—病原生物学]
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参考文献16

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第二军医大学学报
2016年 第2期

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