Efficient Large Scale Syntheses of 3-Deoxy-D-manno-2-octulosonic acid (Kdo) and Its Derivatives
Efficient Large Scale Syntheses of 3-Deoxy-D-manno-2-octulosonic acid (Kdo) and Its Derivatives
复制标题
3-脱氧-D-甘露-2-辛糖酸 (Kdo) 及其衍生物的高效大规模合成
DOI：
10.1021/acs.orglett.5b00901
复制
发表时间：
2015-05-15
期刊：
影响因子：
5.2
通讯作者：
Chai, Yonghai
中科院分区：
文献类型：
--
作者：
Peng, Yingle;Dong, Jie;Chai, Yonghai
提出了一种高效、快速、大规模合成3-脱氧-D-甘露-2-辛酸(KDO)及其衍生物的方法。以D-甘露糖为起始原料，经三步反应制得KDO乙酯的二-O-异丙叉衍生物，一批40g以上，总收率75~80%，无需任何中间体精制。以KDO乙酯的二邻异丙叉衍生物为原料，高产率地快速合成了KDO、KDO甘氨酸酯和2-乙酰化KDO酯。以丁醇为质子源，通过α-异构体的异构化反应，得到了立体选择性较高的2-脱氧-β-Kdo酯。
An efficient method to rapidly synthesize 3-deoxy-D-manno-2-octulosonic acid (Kdo) and its derivatives in large scale has been developed. Starting from D-mannose, the di-O-isopropylidene derivative of Kdo ethyl ester was prepared in three steps on a scale of more than 40 g in one batch in an overall yield of 75-80% without any intermediate purification. Kdo, Kdo glycal, and 2-acetylated Kdo ester were synthesized quickly in high yield from a di-O-isopropylidene derivative of Kdo ethyl ester. 2-Deoxy-beta-Kdo ester was obtained with high stereoselectivity via the epimerization of the alpha-isomer using t-BuOH as a proton source.