Selective Synthesis of Partially Protected D-Talopyranosides and D-Gulopyranosides via Catalytic Asymmetric Dihydroxylation: Multiplier Effects of Substrate Control and Catalyst Control
Selective Synthesis of Partially Protected D-Talopyranosides and D-Gulopyranosides via Catalytic Asymmetric Dihydroxylation: Multiplier Effects of Substrate Control and Catalyst Control
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DOI：
10.1021/acs.orglett.6b03000
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发表时间：
2016-12-02
期刊：
影响因子：
5.2
通讯作者：
Hayashi, Masahiko
中科院分区：
文献类型：
--
作者：
Namito, Yoichi;Michigami, Kyosuke;Hayashi, Masahiko
利用底物控制和催化剂控制的乘数效应，实现了D-吡喃糖苷和D-吡喃葡萄糖苷的高选择性合成。通过O-苯甲酰基保护的底物和AD-mix-beta系统的组合，以96:4的比例获得D-吡喃糖苷。相比之下，通过使用O-叔丁基二甲基甲硅烷基保护的底物和AD-mix-α以3:97的比例获得D-吡喃葡萄糖苷。
Highly selective syntheses of D-talopyranosides and D-gulopyranosides have been achieved by utilizing the multiplier effects of substrate control and catalyst control. Through the combination of an O-benzoyl-protected substrate and the AD-mix-beta system, the D-talopyranoside was obtained in a ratio of 96:4. In contrast, the D-gulopyranoside was obtained in a ratio of 3:97 through the use of an O-tert-butyldimethylsilylprotected substrate and AD -mix-alpha.