Direct and Stereoselective Synthesis of β-D-Mannosides Using 4,6-O-Benzylidene-Protected Mannosyl Diethyl Phosphite as a Donor.
Direct and Stereoselective Synthesis of β-D-Mannosides Using 4,6-O-Benzylidene-Protected Mannosyl Diethyl Phosphite as a Donor.
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DOI：
10.1002/chin.200607205
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发表时间：
2005-11
期刊：
影响因子：
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通讯作者：
Toshifumi Tsuda;Ryoichi Arihara;Shinya Sato;Miyuki Koshiba;Seiichi Nakamura;S. Hashimoto*
中科院分区：
文献类型：
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作者：
Toshifumi Tsuda;Ryoichi Arihara;Shinya Sato;Miyuki Koshiba;Seiichi Nakamura;S. Hashimoto*
摘要介绍了一种直接实用的构建β-甘露糖键的方法。在TMSOTf促进的2,3,4,6-四- o -苄基-d -甘露糖基二乙基亚磷酸酯糖苷化过程中，β-选择性被发现高度依赖于受体醇的反应活性，2,3-二- o -苄基-4 - 6- o -苄基-d -甘露糖基二乙基亚磷酸酯在TMSOTf存在下在CH2Cl2中- 45°C下与多种受体醇反应，产生高收率的β-甘露糖苷，具有良好的β-选择性。
Abstract A direct and practical method for the construction of β-mannosidic linkages is described. While β-selectivities in the TMSOTf-promoted glycosidation of 2,3,4,6-tetra-O-benzyl- d -mannosyl diethyl phosphite are found to be highly dependent on the reactivity of acceptor alcohols, 2,3-di-O-benzyl-4,6-O-benzylidene- d -mannosyl diethyl phosphite reacts with a wide range of acceptor alcohols in the presence of TMSOTf in CH2Cl2 at −45 °C to give β-mannosides in high yields with good to high β-selectivities.