- An efficient and selective 1-N-monoethylation of sisomicin: Process development of netilmicin
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With a new reagent developed for the selective monoethylation at the 1-amino group of sisomicin (1), a new process suitable for the mass production of netilmicin under conditions less sensitive to air and moisture has also been developed. Three of the amino groups, at the C-3, C-2′, and C-6′ positions of the four amino groups of sisomicin, were selectively protected by using Zn(OAc)2 and acetic anhydride in methanol. Development efforts focused on optimising the conditions for ethylation to give an improved product (96% yield) according to the new and concise synthetic route.
- Nam, Ghilsoo,Sung, Hoon Kim,Kim, Joong-Hyup,Shin, Jung-Hyu,Jang, Eun-Sook
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- THE SYNTHESIS OF NETILMICIN via COMPLEXING OF VICINAL AND NON-VICINAL AMINO-HYDROXYL GROUP PAIRS WITH DIVALENT TRANSITION-METAL CATIONS
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Sisomicin was converted into 3,2',6'-tri-N-acetylsisomicin by acetylation of its 3'',4''-vicinal-cis and 1,2''-non-vicinal amino-hydroxyl group pair complex of copper(II) or cobalt(II) acetate.The tri-N-blocked derivative was reductively monoalkylated at the 1-position with acetaldehyde and sodium cyanoborohydride and then N-deprotected to give netilmicin.
- Nagabhushan, Tattanahalli L.,Turner, William N.,Tsai, Hsinghan,Jaret, Robert S.,Schumacher, Doris,et al.
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p. 243 - 250
(2007/10/02)
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- Semisynthetic Aminoglycoside Antibacterials. Part 9. Synthesis of Novel 1- and 3-Substituted and 1- and 3-epi-Substituted Derivatives of Sisomicin and Gentamicin from the 1- and 3-Oxo-derivatives
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The conversion of selectively protected gentamicin and sisomicin derivatives into the 1- and 3-oxo-compounds by reaction with 3,5-di-t-butyl-1,2-benzoquinone is described.By application of suitable reductive techniques these oxo-aminoglucosides have been converted into novel 1- and 3-epi-, 1- and 3-deamino-1- and -3-hydroxy-, 1- and 3-deamino-1- and -3-epi-hydroxy, and 1-deamino-derivatives.A study of the 13C n.m.r. parameters of the 1-epi- and 1-deamino-derivatives has led to the assignment of novel solution conformations for these new aminoglycosides.
- Boxler, Dena L.,Brambilla, Raymond,Davies, D. Huw,Mallams, Alan K.,McCombie, Stuart W.,at al.
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p. 2168 - 2185
(2007/10/02)
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