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• W2159034429 endingPage "1010" @default.
• W2159034429 startingPage "1001" @default.
• W2159034429 abstract "Using leucomycin A5 (1), 3-O-propionylleucomycin A5 (7) was synthesized by the following synthetic route: 2-O-acetylation, 3,9-di-O-trimethylsilylation, 3-O-propionylation, 3,9-di-O-detrimethylsilylation and 2'-O-deacetylation. Acylation of the 3-tertiary hydroxyl group of 2'-O-acetyl-3,9-di-O-trimethylsilylleucomycin A5 with propionyl chloride in the presence of tribenzylamine at 70 degrees C gave a 3-O-propionyl derivative in 96% yield. The structure of the final compound, 3-O-propionylleucomycin A5 (7) was confirmed by means of mass, 1H-NMR and 13C-NMR spectrometry and chemical degradations. 3-O-Propionylleucomycin A5 (7) showed higher antibacterial activity in vitro and higher serum levels than its mother antibiotic. The biological properties of 7 also were compared with those of josamycin and midecamycin." @default.
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• W2159034429 date "1981-01-01" @default.
• W2159034429 modified "2023-10-18" @default.
• W2159034429 title "Acyl derivatives of 16-membered macrolides. I. Synthesis and biological properties of 3-O-propionylleucomycin A5 (TMS-19-Q)." @default.
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• W2159034429 doi "https://doi.org/10.7164/antibiotics.34.1001" @default.
• W2159034429 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/7319915" @default.
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