Synthesis of a library of propargylated and PEGylated α-hydroxy acids toward "clickable" polylactides via hydrolysis of cyanohydrin derivatives.
Synthesis of a library of propargylated and PEGylated α-hydroxy acids toward "clickable" polylactides via hydrolysis of cyanohydrin derivatives.
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DOI：
10.1021/jo5016135
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发表时间：
2014-10-17
期刊：
影响因子：
--
通讯作者：
Baker GL
中科院分区：
文献类型：
--
作者：
Zhang Q;Ren H;Baker GL
描述了一种新的简单实用的方法，用于可扩展地合成一种新的丙烯酸化和聚乙二醇化α-羟基酸库，以制备“可点击”的聚乳酸。以容易获得的炔丙醇、溴乙醛二乙缩醛、邻苯二甲酸乙二醇酯或聚乙二醇乙二醇酯为原料，合成工艺简便，成本低，不需要柱层析纯化。末端炔的官能团来自于相应的容易获得的氰醇衍生物在甲醇硫酸中的水解。简单的去对称化、单官能化和高效的链延长偶联进一步使有机葡萄糖能够以简单有效的方式结合到α-羟基酸中。最后，烯丙氧基乳酸的合成表明，烯基也与所开发的方法相容。
A new simple and practical protocol for scalable synthesis of a novel library of propargylated and PEGylated α-hydroxy acids toward the preparation of “clickable” polylactides was described. The overall synthesis starting from readily available propargyl alcohol, bromoacetaldehyde diethyl acetal, and OEGs or PEGs was developed as a convenient procedure with low cost and no need of column chromatographic purification. The terminal alkyne functionality survives from hydrolysis of the corresponding easily accessible cyanohydrin derivatives in methanolic sulfuric acid. Facile desymmetrization, monofunctionalization, and efficient chain-elongation coupling of OEGs further enable the incorporation of OEGs to α-hydroxy acids in a simple and efficient manner. At the end, synthesis of allyloxy lactic acid indicates that an alkene group is also compatible with the developed method.
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影响因子：
5.2
作者：
Huang, Baohua;Desai, Ankur;Tang, Shengzhuang;Thomas, Thommey P.;Baker, James R., Jr.
通讯作者：
Baker, James R., Jr.
影响因子：
4.3
作者：
Asakawa, M;Ashton, PR;Venturi, M
通讯作者：
Venturi, M
影响因子：
5.5
作者：
Chan, Justin W.;Shin, Jungwhan;Lowe, Andrew B.
通讯作者：
Lowe, Andrew B.
影响因子：
14
作者：
Claes, LE;Ignatius, AA;Scholz, C
通讯作者：
Scholz, C
影响因子：
5.5
作者：
Fairbanks, Benjamin D.;Sims, Evan A.;Bowman, Christopher N.
通讯作者：
Bowman, Christopher N.