Johnsson Richard, Mani Katrin, Cheng Fang, Ellervik Ulf
Organic Chemistry, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
J Org Chem. 2006 Apr 28;71(9):3444-51. doi: 10.1021/jo0526284.
Regioselective reductive openings of mixed phenolic-benzylic acetals, using BH3.NMe3-AlCl3, was investigated, and a mechanism where the outcome is directed by the electrostatic potential of the two oxygen atoms is presented. The regioselective acetal opening was used in the synthesis of a fluorescently labeled analogue to antiproliferative xylosides. The fluorescently labeled xyloside was tested for uptake, antiproliferative activity, and glycosaminoglycan priming in different cell lines. The xyloside was taken up by all cell lines but did not initiate glycosaminoglycan biosynthesis.
研究了使用BH₃·NMe₃-AlCl₃对混合酚醛-苄基缩醛进行区域选择性还原开环反应，并提出了一种由两个氧原子的静电势决定反应结果的机理。区域选择性缩醛开环反应被用于合成抗增殖木糖苷的荧光标记类似物。对该荧光标记木糖苷在不同细胞系中的摄取、抗增殖活性和糖胺聚糖引发作用进行了测试。该木糖苷被所有细胞系摄取，但未引发糖胺聚糖生物合成。
