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一种基于氨基葡萄糖的新型手性β-氨基醇的合成

Synthesis of a New Kind of Chiral β-Amino Alcohol Based on Glucosamine
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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.以氨基葡萄糖为原料设计合成一种新型手性β-氨基醇.氨基葡萄糖盐酸盐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.4步反应总收率35%,对目标化合物及反应中间体的结构均进行1H NMR表征. Chiral amino alcohol is widely used in a variety of asymmetric reactions as catalysts.A new kind of chiral β-amino alcohol,methyl 4,6-O-benzylidenen-2-deoxy-2-amino-α-D-glucopyranoside,was synthesized by a four-step reaction starting from D-glucosamine hydrochloride commercially available.Firstly,D-glucosamine hydrochloride was condensed with methyl chloroformate under the catalyst of sodium carbonate.Then,the obtained product underwent methylation,benzylidene protection,and alkaline hydrolysis successively.The total yield was 35%,and the target compound and the key intermediates were characterized by^1 H NMR.
作者 施梅
机构地区 南京晓庄学院生物化工与环境工程学院
出处 《南京晓庄学院学报》 2014年第6期44-46,共3页 Journal of Nanjing Xiaozhuang University
基金 南京晓庄学院自然科学项目(2011NXY19)
关键词 Β-氨基醇 氨基葡萄糖 手性 合成 β-amino alcohol glucosamine chiral synthesis
分类号 O621.3 [理学—有机化学]
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参考文献12

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南京晓庄学院学报
2014年 第6期

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