264128-06-5Relevant articles and documents
Synthesis of 4′/5′-Spirocyclopropanated Uridine and d -Xylouridine Derivatives and Their Activity against the Human Respiratory Syncytial Virus
K?llmann, Christoph,Wiechert, Svenja M.,Jones, Peter G.,Pietschmann, Thomas,Werz, Daniel B.
, p. 6966 - 6971 (2019)
The Simmons-Smith-Furukawa reaction was used to generate 4′/5′-spirocyclopropanated uridine analogs from electron-rich exocyclic enol esters. During synthesis, the native hydroxylation pattern of the nucleoside is preserved and offers the possibility for a late stage 5′-phosphorylation at the spirocyclopropanol moiety. All synthesized spirocyclopropanated uridine derivatives, including the corresponding 5′-monophosphate (cpUMP), were evaluated with respect to their antiviral activity in an HRSV assay showing moderate, but promising activity.
Total Synthesis of Caprazamycin A: Practical and Scalable Synthesis of syn-β-Hydroxyamino Acids and Introduction of a Fatty Acid Side Chain to 1,4-Diazepanone
Nakamura, Hugh,Tsukano, Chihiro,Yoshida, Takuma,Yasui, Motohiro,Yokouchi, Shinsuke,Kobayashi, Yusuke,Igarashi, Masayuki,Takemoto, Yoshiji
, p. 8527 - 8540 (2019/06/04)
The first total synthesis of caprazamycin A (1), a representative liponucleoside antibiotic, is described. Diastereoselective aldol reactions of aldehydes 12 and 25-27, derived from uridine, with diethyl isocyanomalonate 13 and phenylcarbamate 21 were investigated using thiourea catalysts 14 or bases to synthesize syn-β-hydroxyamino acid derivatives. The 1,4-diazepanone core of 1 was constructed using a Mitsunobu reaction, and the fatty acid side chain was introduced using a stepwise sequence based on model studies. Notably, global deprotection was realized using palladium black and formic acid without hydrogenating the olefin in the uridine unit.
Novel carbohydrate scaffolds. Assembly of a uridine-mannose scaffold based on tunicamycin
Silva, Domingos J.,Sofia, Michael J.
, p. 855 - 858 (2007/10/03)
A disaccharide scaffold based on tunicamycin was synthesized from D- uridine and L-mannose. The key step in disaccharide assembly was a β- mannosylation performed using Crich's modification of the sulfoxide glycosylation method. The scaffold described contains two orthogonal derivatization sites and will be used in the search for novel biologically active compounds. (C) 2000 Elsevier Science Ltd.
