（1→6）-分支（1→3）-葡萄糖六糖含甘露糖类似物的合成
Synthesis of mannose-containing analogues of (1-->6)-branched (1-->3)-glucohexaose.
作者信息
Wu Zicheng, Kong Fanzuo
机构信息
Research Center for Eco-Environmental Sciences, Academia Sinica, P.O. Box 2871, 100085, Beijing, China.
出版信息
Carbohydr Res. 2004 Jan 22;339(2):377-84. doi: 10.1016/j.carres.2003.10.015.
Coupling of the trisaccharide acceptor 2,4,6-tri-O-acetyl-beta-D-glucopyranosyl-(1-->3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1-->6)]-5-O-acetyl-1,2-O-isopropylidene-alpha-D-glucofuranose (2) with the trisaccharide donor 2,3,4,6-tetra-O-benzoyl-alpha-D-annopyranosyl-(1-->3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1-->6)]-2,4-di-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (1) gave an alpha-linked hexasaccharide 3, while coupling of 2 with the trisaccharide donor 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->3)-[2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)]-2,4-di-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (7) produced alpha- 8 and beta-linked 12 hexasaccharides in a ratio of 3:2. Deprotection of 3, 8, and 12 afforded the analogues of the immunomodulator beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-D-Glcp (A).
三糖受体2,4,6 - 三 - O - 乙酰基 - β - D - 吡喃葡萄糖基 - (1→3)-[2,3,4,6 - 四 - O - 苯甲酰基 - β - D - 吡喃葡萄糖基 - (1→6)]-5 - O - 乙酰基 - 1,2 - O - 异亚丙基 - α - D - 呋喃葡萄糖 (2) 与三糖供体2,3,4,6 - 四 - O - 苯甲酰基 - α - D - 吡喃甘露糖基 - (1→3)-[2,3,4,6 - 四 - O - 苯甲酰基 - β - D - 吡喃葡萄糖基 - (1→6)]-2,4 - 二 - O - 乙酰基 - α - D - 吡喃葡萄糖基三氯乙酰亚胺酯 (1) 偶联得到α - 连接的六糖3，而2与三糖供体2,3,4,6 - 四 - O - 苯甲酰基 - α - D - 吡喃甘露糖基 - (1→3)-[2,3,4,6 - 四 - O - 苯甲酰基 - α - D - 吡喃甘露糖基 - (1→6)]-2,4 - 二 - O - 乙酰基 - α - D - 吡喃葡萄糖基三氯乙酰亚胺酯 (7) 偶联则以3:2的比例生成α - 连接的六糖8和β - 连接的六糖12。对3、8和12进行脱保护得到免疫调节剂β - D - 葡萄糖吡喃糖基 - (1→3)-[β - D - 葡萄糖吡喃糖基 - (1→6)]-α - D - 葡萄糖吡喃糖基 - (1→3)-β - D - 葡萄糖吡喃糖基 - (1→3)-[β - D - 葡萄糖吡喃糖基 - (1→6)]-D - 葡萄糖 (A) 的类似物。
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