| 保护的β-2-脱氧-2-氨基葡三糖的合成 |
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| 引用本文： | 郭振楚,熊兴泉.保护的β-2-脱氧-2-氨基葡三糖的合成[J].有机化学,2005,25(11):1437-1441. |
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| 作者姓名： | 郭振楚 熊兴泉 |
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| 作者单位： | 1. 湖南科技大学化学化工学院,湘潭,411201
2. 湖南科技大学化学化工学院,湘潭,411201;中国科学院化学研究所,北京,100080 |
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| 基金项目： | 湖南省重点学科建设项目 |
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| 摘 要： | 以茴香醛保护氨基方法得到的β-构型的四乙酰基氨基葡萄糖盐酸盐(1)为原料, 采用三氯乙酰基(TCA)、三氯乙酰亚胺酯基(TCI)和乙硫基(SEt)保护体系, 经五步反应以产率40.5%得到完全β-构型保护的β-(1→3)-2-脱氧-2-氨基葡二糖7, 又经两步合成得到保护的β-(1→3)-2-脱氧-2-氨基葡二糖受体8, 共八步合成了保护的β-(1→3)-2-脱氧-2-氨基葡三糖10, 总产率为27%. 以上化合物均为未知. 同时, 还得到了用以合成β-(1→4)-保护的氨基葡四糖的受体6. 采用该保护体系可以高选择性地、较高产率地合成氨基寡糖.
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| 关 键 词： | 氨基葡萄糖盐酸盐 2-脱氧-2-氨基葡三糖 三氯乙酰氯 三氯乙酰亚胺酯 乙硫醇 |
| 收稿时间： | 09 27 2004 12:00AM |
| 修稿时间： | 05 11 2005 12:00AM |
Synthesis of Protected 2-Amino-2-deoxytriglucose |
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| GUO,Zhen-Chu,XIONG,Xing-Quan.Synthesis of Protected 2-Amino-2-deoxytriglucose[J].Chinese Journal of Organic Chemistry,2005,25(11):1437-1441. |
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| Authors: | GUO Zhen-Chu XIONG Xing-Quan |
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| Institution: | a.College of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201;b.Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080 |
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| Abstract: | By using trichloroacetyl, trichloroacetimidate group and ethylthio as the protection system and through five steps, protected β-(1→3)-2-amino-2-deoxydiglucose 7 was synthesized from β-tetra-O-acetyl-glucosylamine hydrochloride (1). β-(1→3)-2-amino-2-deoxydiglucose acceptor 8 was also produced by two steps. Finally protected β-(1→3)-2-amino-2-deoxytriglucose 10 was obtained through eight steps with the tolal yield of 27%. These compounds are all new ones. Using this protection system, amino- oligosaccharides can be selectively synthesized with high yield. |
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| Keywords: | glucosylamine hydrochloride 2-amino-2-deoxyl-triglucose trichloroacetyl chloride trichloroacetimidate ethanethiol |
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