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基于D-葡糖胺的手性β-氨基醇的合成
Synthesis of chiral β-amino alcohols based on D-glucosamine
【摘要】 手性氨基醇作为催化剂广泛应用于多种不对称合成反应中。以D-葡糖胺为原料设计合成一系列新型手性β-氨基醇。D-葡糖胺首先与氯甲酸甲酯缩合,再先后经过甲基化、苄叉保护、碱性水解反应,得4,6-O-苄叉基-2-脱氧-2-氨基-α-D-吡喃葡萄糖甲苷,进一步将其通过N-烃化反应或N-磺酰化反应合成得手性β-氨基醇。产物结构经1H NMR,13C NMR和MS表征确证。
【Abstract】 Chiral amino alcohols were widely used in a variety of asymmetric reactions as catalysts. A series of novel chiral β-amino alcohols were synthesized by a five-step reaction starting from commercially available D-glucosamine. Firstly,D-glucosamine condensed with methyl chloroformate under the catalyst of sodium carbonate. Then,the product of the previous step underwent methylation,benzylidene protection,alkaline hydrolysis and N-alkylation or N-sulfonylation successively. The target compounds and the key intermediates were characterized by1 H NMR,13 C NMR and MS.
- 【文献出处】 化学研究与应用 ,Chemical Research and Application , 编辑部邮箱 ,2015年01期
- 【分类号】O621.3
- 【被引频次】3
- 【下载频次】132