Efficient Large Scale Syntheses of 3-Deoxy-d-manno-2-octulosonic acid (Kdo) and Its Derivatives,Organic Letters

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Efficient Large Scale Syntheses of 3-Deoxy-d-manno-2-octulosonic acid (Kdo) and Its Derivatives
Organic Letters ( IF 4.9 ) Pub Date : 2015-04-30 00:00:00 , DOI: 10.1021/acs.orglett.5b00901
Yingle Feng ₁ , Jie Dong ₁ , Fangyuan Xu ₁ , Aiyun Liu ₁ , Li Wang ₁ , Qi Zhang ₁ , Yonghai Chai ₁

Affiliation

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-β-Kdo ester was obtained with high stereoselectivity via the epimerization of the α-isomer using t-BuOH as a proton source.

中文翻译：

有效的大规模合成3-Deoxy-d-manno-2-octulosonic acid（Kdo）及其衍生物

快速高效的方法合成3-脱氧d -manno -2-辛酮糖酸（KDO）及其在大规模衍生物已被开发。从d-甘露糖开始，分三批以超过40 g的规模分三步制备Kdo乙酯的二-O-异亚丙基衍生物，总产率为75-80％，无需任何中间纯化。由Kdo乙酯的二-O-异亚丙基衍生物快速高产率地合成了Kdo，Kdo糖基和2-乙酰化的Kdo酯。通过使用t - BuOH作为质子源，通过α-异构体的差向异构化，以高立体选择性获得2-脱氧-β-Kdo酯。

更新日期：2015-04-30

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