| Highly Efficient Regio- and Stereoselective Synthesis of β-（1 →6）-Branched β-（1 →3）-Linked Glucohexaose and Its Analogue |
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| 引用本文： | 衣悦涛 赵前飞 钱凤珍 宁君. Highly Efficient Regio- and Stereoselective Synthesis of β-（1 →6）-Branched β-（1 →3）-Linked Glucohexaose and Its Analogue[J]. 中国化学, 2007, 25(3): 385-389. DOI: 10.1002/cjoc.200790074 |
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| 作者姓名： | 衣悦涛 赵前飞 钱凤珍 宁君 |
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| 作者单位： | [1]Research Center for Eco-environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China [2]China University of Mining and Technology, Beijing 100083, China |
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| 基金项目： | Project supported by the Major State Basic Research Development Program of China （No. 2006CB 101907）. |
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| 摘 要： | A β-（1→）6）-branched β-（1→）3）-linked glucohexaose （1） and its lauryl glycoside （2）, present in many biologically active polysaccharides from traditional herbal medicines such as Ganoderma lucidum, Schizophyllum commune and Lentinus edodes, were highly efficiently synthesized. Coupling of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- （1--）3）-2-O-benzoyl-4,6-O-benzylidene-a-D-glucopyranosyl trichloroacetimidate （7） with 3,6-branched acceptors 8 and 12 gave β-（1→）3）-linked pentasaccharides （9） and （13）, then via simple chemical transformation 4＇,6＇-OH pentasaccharide acceptors 10 and 14 were obtained. Regio- and stereoselective coupling of 3 with 10 and 14 gave β-（1→）3）-linked hexasaccharides （11） and （15） as the major products. Deprotection of 11 and 15 provided the target sugar 1 and 2. Thus, a new method for the preparation of this kind of compounds was developed.
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| 关 键 词： | β-（1→）6）支链β-（1→）3）-链接葡糖-己糖 月桂酸糖苷 类似物 区域-立体选择性合成 抗肿瘤活性 |
| 修稿时间： | 2006-03-202006-11-01 |
Highly Efficient Regio‐ and Stereoselective Synthesis of β‐(1→6)‐Branched β‐(1→3)‐Linked Glucohexaose and Its Analogue |
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| YI Yue-Tao, ZHAO Qian-Fei, QIAN Feng-Zhen, NING Jun. Highly Efficient Regio‐ and Stereoselective Synthesis of β‐(1→6)‐Branched β‐(1→3)‐Linked Glucohexaose and Its Analogue[J]. Chinese Journal of Chemistry, 2007, 25(3): 385-389. DOI: 10.1002/cjoc.200790074 |
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| Authors: | YI Yue-Tao ZHAO Qian-Fei QIAN Feng-Zhen NING Jun |
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| Affiliation: | a Research Center for Eco-environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China; b China University of Mining and Technology, Beijing 100083, China |
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| Abstract: | A β‐(1→6)‐branched β‐(1→3)‐linked glucohexaose ( 1 ) and its lauryl glycoside ( 2 ), present in many biologically active polysaccharides from traditional herbal medicines such as Ganoderma lucidum, Schizophyllum commune and Lentinus edodes, were highly efficiently synthesized. Coupling of 2,3,4,6‐tetra‐O‐benzoyl‐β‐D‐glucopyranosyl‐ (1→3)‐2‐O‐benzoyl‐4,6‐O‐benzylidene‐α‐D‐glucopyranosyl trichloroacetimidate ( 7 ) with 3,6‐branched acceptors 8 and 12 gave β‐(1?3)‐linked pentasaccharides ( 9 ) and ( 13 ), then via simple chemical transformation 4′,6′‐OH pentasaccharide acceptors 10 and 14 were obtained. Regio‐ and stereoselective coupling of 3 with 10 and 14 gave β‐(1→3)‐linked hexasaccharides ( 11 ) and ( 15 ) as the major products. Deprotection of 11 and 15 provided the target sugar 1 and 2 . Thus, a new method for the preparation of this kind of compounds was developed. |
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| Keywords: | gluco-hexasaccharide antitumor activity regio- and stereoselective synthesis |
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