Regioselective synthesis of 2-O-acyl-3-O-(1-acyloxyalkyl) prodrugs of 5,6-isopropylidene-l-ascorbic acid
作者:John Prybylski、Nikki A. Thiele、Kenneth B. Sloan
DOI:10.1016/j.tetlet.2016.02.112
日期:2016.4
An efficient regioselective synthesis of 2-O-acyl-3-O-(1-acyloxyalkyl) prodrugs of vitamin C 5,6-acetonide has been developed which does not involve tedious column chromatographic separation of the desired products from contaminants exhibiting very similar Rf values. Vitamin C 5,6-acetonide is first acylated with one equivalent of acyl halide in the presence of two equivalents of pyridine. The crude
已经开发出有效的区域选择性合成维生素C 5,6-丙酮化物的2 - O-酰基-3- O-(1-酰氧基烷基)前药的方法,该方法不涉及将所需产物与表现出非常相似R的污染物进行繁琐的柱色谱分离。f值。首先在两当量的吡啶存在下,先用一当量的酰基卤将维生素C 5,6-丙酮化物酰化。然后在一当量的三乙胺的存在下,用一当量的1-酰氧基烷基-1-碘化物将2- O-酰化的粗产物烷基化。2- Ô酰基-3- Ö - (1-酰氧基)维生素C 5,6-丙酮化在中等产率获得。