- Synthesis method of isepamicin
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The invention discloses a synthesis method of isepamicin, which comprises the following steps: taking gentamicin B as a raw material, reacting with a metal chelating agent and (Boc) 2O to obtain an intermediate P1, esterifying the intermediate P1 and Boc-(S)-isoserine to obtain an intermediate P2, and carrying out acidolysis deprotection on the intermediate P2 to obtain isepamicin. Both the intermediate P1 and the intermediate P2 are refined in a recrystallization mode, purification through an ion exchange column chromatography separation method in the prior art is replaced, the synthesis method is easy to operate, short in period, little in waste liquid and easy for industrial production, the prepared isepamicin is high in purity, and the synthesis route of the isepamicin is as follows: the synthesis route of the isepamicin is shown in the specification.
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- New convenient reagents for chemoselective N-alkoxycarbonylation of (S)-isoserine: Application in the isepamicin synthesis
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A synthesis of a series of N-alkoxycarbonyl mercaptobenzothiazoles (MBTs) and their application as reagents for chemoselective protection of amino group are presented herein. It was shown that all new reagents, Z-MBT, Fmoc-MBT, Phoc-MBT, and Tec-MBT, are highly effective in the selective N-alkoxycarbonylation of (S)-isoserine. The transformation is a simple, fast, and low-cost protocol, which is applicable in scale-up experiments. The starting MBT was fully recovered at the end of the process, which is an additional advantage of the method. The efficiency of the Z-reagent was also demonstrated by the selective protection of both gentamicin B and (S)-isoserine before their peptide-type coupling in the synthesis of the aminoglycoside antibiotic isepamicin. Copyright Taylor & Francis Group, LLC.
- Doktorov, Konstantin,Tarpanov, Velichko,Mechkarova, Pepa
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p. 3709 - 3718
(2008/02/10)
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- A semisynthesis of isepamicin by fragmentation method
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Garamine derivative, key intermediate, was obtained from acid cleavage of sisomicin derivative. Its subsequent product was glycosylated with 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-d-glucopyranosyl chloride using silver triflate as a promoter to give isepamicin.
- Moon, Man Sik,Jun, Sook Jin,Lee, So Ha,Cheong, Chan Seong,Kim, Kwan Soo,Lee, Byung Suk
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p. 607 - 609
(2007/10/03)
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