Alternative synthesis and antibacterial evaluation of 1,5-dideoxy-1,5-imino-L-rhamnitol
Alternative synthesis and antibacterial evaluation of 1,5-dideoxy-1,5-imino-L-rhamnitol
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DOI：
10.1016/j.carres.2015.10.015
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发表时间：
2016-01-01
影响因子：
3.1
通讯作者：
Crich, David
中科院分区：
文献类型：
--
作者：
Dharuman, Suresh;Wang, Yichen;Crich, David
以鼠李糖为原料，7步合成了5-叠氮-5-脱氧-2,3- o-异丙基-鼠李糖呋喃糖，总收率为17%。该合成方法的一个关键特点是在半缩醛存在的情况下，用Parikh-Doering试剂选择性氧化2,3- o -异丙基-l-鼠李糖中的仲醇，得到相应的酮，产率高。然后根据文献方案将5-叠氮-5-脱氧-2,3- o-异丙基-l-鼠李糖呋喃糖转化为1,5-二脱氧-1,5-亚胺-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。(C) 2015 Elsevier Ltd.版权所有。
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-iminol-rhamnitol, which was found to have no significant antimicrobial activity against Pseudomonas aeruginosa, methicillin-resistant Staphylococcus aureus, and Escherichia coli. (C) 2015 Elsevier Ltd. All rights reserved.