期刊
CARBOHYDRATE RESEARCH
卷 419, 期 -, 页码 29-32出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2015.10.015
关键词
L-1-deoxyrhamnojirimycin; Pseudomonas aeruginosa; L-rhamnofuranose; Glycosyl transferase inhibitors; Antibacterial
资金
- NIH [GM62160]
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.
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