Dharuman Suresh, Wang Yichen, Crich David
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202, USA.
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202, USA.
Carbohydr Res. 2016 Jan;419:29-32. doi: 10.1016/j.carres.2015.10.015. Epub 2015 Nov 4.
A convenient synthesis is described of 5-azido-5-deoxy-2,3-O-isopropylidene-L-rhamnofuranose from L-rhamnose in seven steps and 17% overall yield. A key feature of the synthesis is the selective oxidation of the secondary alcohol in 2,3-O-isopropylidene-L-rhamnofuranose in the presence of the hemiacetal to give the corresponding ketone in good yield using the Parikh-Doering reagent. 5-Azido-5-deoxy-2,3-O-isopropylidene-l-rhamnofuranose is then converted by a literature protocol to 1,5-dideoxy-1,5-imino-L-rhamnitol, which was found to have no significant antimicrobial activity against Pseudomonas aeruginosa, methicillin-resistant Staphylococcus aureus, and Escherichia coli.
描述了一种从L-鼠李糖出发，经七步反应以17%的总收率方便地合成5-叠氮基-5-脱氧-2,3-O-异亚丙基-L-鼠李呋喃糖的方法。该合成方法的一个关键特征是在半缩醛存在下，使用帕里什-多林试剂选择性氧化2,3-O-异亚丙基-L-鼠李呋喃糖中的仲醇，以良好的收率得到相应的酮。然后按照文献方法将5-叠氮基-5-脱氧-2,3-O-异亚丙基-L-鼠李呋喃糖转化为1,5-二脱氧-1,5-亚氨基-L-鼠李糖醇，发现其对铜绿假单胞菌、耐甲氧西林金黄色葡萄球菌和大肠杆菌没有显著的抗菌活性。
