Enzymatic desymmetrization of a meso polyol corresponding to the C(19)-C(27) segment of rifamycin S
Enzymatic desymmetrization of a meso polyol corresponding to the C(19)-C(27) segment of rifamycin S
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DOI：
10.1021/jo991437w
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发表时间：
2000-03-24
影响因子：
3.6
通讯作者：
Rose, YS
中科院分区：
文献类型：
--
作者：
Chênevert, R;Rose, YS
在猪胰腺脂肪酶存在下，内消旋多元醇 2 通过乙酸乙烯酯（溶剂和酰基供体）进行立体选择性酰化，以良好的产率 (76%) 和高对映体纯度 (ee > 98%) 得到相应的单酯 5。酶促反应对于伯醇端基也具有高度区域选择性，并且不涉及两种未保护的仲醇。化合物 5 对应于利福霉素 S 的 C(19)-C(27) 片段。
The stereoselective acylation of meso polyol 2 by vinyl acetate (solvent and acyl donor) in the presence of porcine pancreas lipase gave the corresponding monoester 5 in good yield (76%) and high enantiomeric purity (ee > 98%). The enzymatic reaction was also highly regioselective for a primary alcohol end group, and the two unprotected secondary alcohols were not involved. Compound 5 corresponds to the C(19)-C(27) fragment of rifamycin S.