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Synthesis of Arrays Using Low Molecular Weight MPEG-Assisted Mitsunobu Reaction

ACS combinatorial science(2011)SCI 3区

Univ Glasgow | GSK Med Ctr

Cited 17|Views13
Abstract
Triphenylphosphine tagged with a short poly(ethyleneglycol)-ω-monomethyl ether chain (light MPEG, 10−16 ethylenoxy units, MTPP-G2) and an MPEG-tagged version of diethyl azodicarboxylate (MDEAD) have been used to prepare a 20 member library of esters, ethers, and sulfonamides, with cLogP’s in the range of 1.4−5.7 on a 0.1 mmol scale. Removal of MPEG-tagged side products was achieved by MPEG-assisted solid-phase extraction (MSPE) on prepacked silica columns to give the products in good yield and high purity.
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triphenylphosphine,Mitsunobu reaction,cLogP,solid-phase extraction
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要点】:该论文提出了一种使用低分子量MPEG辅助的Mitsunobu反应合成阵列的新方法,通过MTPP-G2和MDEAD制备了20个成员的酯、醚和磺酰胺库,并利用MPEG辅助的固相萃取技术实现了产物的高纯度分离。

方法】:研究利用带有短聚乙二醇链的磷酸三苯酯(MTPP-G2)和带有MPEG标签的偶氮二羧酸二乙酯(MDEAD)进行Mitsunobu反应,合成了具有不同cLogP值的有机化合物库。

实验】:实验在0.1 mmol的规模上进行,使用MPEG辅助的固相萃取(MSPE)技术对预装硅胶柱进行产物纯化,得到了高产率和高质量的产品,数据集名称未在文本中提及。