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首页> 外文期刊>Proceedings of the National Academy of Sciences of the United States of America >Cyclic esters and cyclodepsipeptides derived from lactide and 2,5-morpholinediones
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Cyclic esters and cyclodepsipeptides derived from lactide and 2,5-morpholinediones

机译：丙交酯和2,5-吗啉二酮衍生的环酯和环二肽

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摘要

The reaction between (BuLi)-Li-n in benzene and the solid polystyrene support PS-C6H4CH2NH2 leads to a lithiated species that can be represented as PS-C6H4CH2NHLi(LiBu).,, where x similar to 4, which is active in the ring-opening of the cyclic esters L-lactide, rac-lactide, and 25-morpholinediones. With approximate to 10 eq of these monomeric six-membered rings and with heating, cyclic esters (MeCHC(0)0), and [MeCHC(O)OCHRC(NH)O](n) are reversibly released to the solution. These have been characterized by electrospray ionization MS, and some small rings have been separated by gel-permeation chromatography. Addition of NaBPh4 to a heated benzene solution containing these rings preferentially removes the 18-membered rings from solution. For lactide this is shown to form the basis for chemical amplification from a dynamic combinatorial library and lactide can be converted to (MeCHC(0)0)6 in > 80% yield. Metallated supports derived from Me2Mg and Et2Zn are less reactive but do show some ability for lactide ring-enlarging. The 18-membered ring (R,R,R,S,S,S)- and meso-(R,S,R,S,R,S)-(MeCHC(0)0)6 and the 24-membered ring (MeCHC(O)(OCHPrC)-C-i(NH)0)4 have been characterized by single-crystal x-ray diffraction studies, together with the complex Na[eta(3) -S,S,S,S,S,S-(MeCHC(O)O)(6)](2)BPh4.
机译：苯中的（BuLi）-Li-n与固体聚苯乙烯载体PS-C6H4CH2NH2之间的反应会生成锂化物质，可以表示为PS-C6H4CH2NHLi（LiBu）。其中x与4相似，在环状酯L-丙交酯，rac-丙交酯和25-吗啉二酮的开环。在这些单体六元环大约10 eq的情况下，在加热的情况下，环状酯（MeCHC（0）0）和[MeCHC（O）OCHRC（NH）O]（n）可逆地释放到溶液中。这些已通过电喷雾电离质谱仪进行了表征，并且一些小环已通过凝胶渗透色谱分离。将NaBPh4添加到含有这些环的加热苯溶液中时，会优先从溶液中除去18元环。对于丙交酯，这表明构成了从动态组合库进行化学扩增的基础，丙交酯可以> 80％的产率转化为（MeCHC（0）0）6。衍生自Me2Mg和Et2Zn的金属化载体反应性较低，但确实表现出一定的丙交酯环扩大能力。 18元环（R，R，R，S，S，S）-和内消旋-（R，S，R，S，R，S）-（MeCHC（0）0）6和24元环（MeCHC（O）（OCHPrC）-Ci（NH）0）4已通过单晶X射线衍射研究以及复合物Na [eta（3）-S，S，S，S，S， S-（MeCHC（O）O）（6）]（2）BPh4。

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