9-FLUORENYLMETHOXYCARBONYL AMINO-PROTECTING GROUP
9-FLUORENYLMETHOXYCARBONYL AMINO-PROTECTING GROUP
复制标题
DOI：
10.1021/jo00795a005
复制
发表时间：
1972-01-01
影响因子：
3.6
通讯作者：
HAN, GY
中科院分区：
文献类型：
--
作者：
CARPINO, LA;HAN, GY
最常用的氨基保护基团是那些在各种酸性条件下解封的基团。1到目前为止，还没有在温和、碱性、非水解性条件下可以快速裂解的酰胺或氨基甲酸酯官能团，尽管已知有几个保护基可以被碱性试剂裂解。邻苯二甲酰基2在乙醇28中被肼重新移动(或最近通过使用甲胺2b水溶液)，三氟乙酰基被稀碱重新移动。3用强水碱或乙醇钠裂解/3-对甲苯磺酰乙氧羰基，4 5a裂解过程，其性质在一定程度上与本文所述的方法相一致。这项工作起源于Crowley 6的观察，即Carbanilate 2来自3，3，3-三氯-L-硝基-2-丙醇(L)7
The amino-protecting groups which are most com-monly used are those which are deblocked under various acidic conditions. 1 Heretofore no amide or urethane function has been available which could be rapidly cleaved under mild, alkaline, nonhydrolytic conditions, although several protective groups are known to be cleaved by basic reagents. The phthaloyl group2 is re-moved by hydrazine in ethanol28 (or more recently by the use of aqueous methylamine2b), and the trifluoroacetyl group by dilute aqueous alkali. 3 Strong aqueous alkali or sodium ethoxide has been used to cleave the/3-tosyl-ethyloxycarbonyl group, 4 5a cleavage process the nature of which anticipates to some extent the method de-scribed in the present paper. This work originated in the observation ofCrowley6 that the carbanilate 2 derived from 3, 3, 3-trichIoro-l-nitro-2-propanol (l) 7