Regioselective One-Pot Benzoylation of Triol and Tetraol Arrays in Carbohydrates
Regioselective One-Pot Benzoylation of Triol and Tetraol Arrays in Carbohydrates
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碳水化合物中三醇和四醇阵列的区域选择性一锅苯甲酰化
DOI：
10.1021/acs.orglett.8b01446
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发表时间：
2018
期刊：
影响因子：
5.2
通讯作者：
Peng Peng
中科院分区：
文献类型：
--
作者：
Li Tong;Li Tianlu;Cui Tongxiao;Sun Yajing;Wang Fengshan;Cao Hongzhi;Schmidt Richard R;Peng Peng
以BzCN和DMAP/DIPEA为碱基的2,3,4- o无保护α-半乳苷和α-岩藻皮苷保护可直接和区域选择性地产生3- o无保护衍生物。这些研究的基本原理是利用“氰化物效应”和“烷氧基介导的二醇效应”的最终协同作用。这样，即使完全不受保护的α-半乳糖苷也可以选择性地转化为相应的2,4,6- o保护衍生物。这些构建块的巨大效用在有效的三糖合成中得到了证明。
Protection of 2,3,4-O-unprotected α-galacto- and α-fucopyranosides with BzCN and DMAP/DIPEA as the base afforded directly and regioselectively the 3-O-unprotected derivatives. The rationale for these studies was to take advantage of the eventual cooperativity of the “cyanide effect” and “the alkoxy group mediated diol effect”. This way, even the totally unprotected α-galactopyranosides could be regioselectively transformed into the corresponding 2,4,6-O-protected derivatives. The great utility of these building blocks was demonstrated in efficient trisaccharide syntheses.