- Method for synthesizing arab League Beica starbeica star and
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The present invention relates to a method for synthesizing dibekacin and arbekacin. The method comprises: using kanamycin B as an initial raw material, protecting five amino groups of the kanamycin B by using t-butyloxycarboryl, protecting hydroxyl of positions 4''and 6'' by aldol condensation, eliminating, in the presence of 2,4,5-triiodo-imidazol, triphenylphosphine, and imidazole, hydroxyl of positions 3' and 4' to form a double bond, removing the protection of the amino groups and the hydroxyl in a hydrochloric methanol solution, and performing catalytic hydrogenation to obtain dibekacin; and using 3',4'-didanosine-3', 4'-didehydro-kanamycin B as a raw material, protecting all the amino groups and hydroxyl by using trimethylsilyl acetate, acylating an amino group of a position 1 by using synthesized active ester, removing the protected groups by sequentially using hydrochloric acid and hydrazine hydrate, and finally, performing catalytic hydrogenation to obtain arbekacin. The synthesizing method is simple in operation, high in yield, environmentally-friendly, low in production cost, and beneficial to industrial production.
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Paragraph 0079
(2017/01/19)
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- Semisynthetic Aminoglycoside Antibacterials. Part 7. Synthesis of Novel Hexopyranosyl and Hexofuranosyl Derivatives of Gentamine C1 and C1a
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Acidic hydrolysis of gentamicin C1 and C1a provides ready access to the pseudodisaccharides gentamine C1 and C1a respectively.Glycosylation of tetrakis-N-benzyloxycarbonylgentamine C1 and C1a using the Koenigs-Knorr or Lemieux-Nagabhushan reactions has led to the preparation of a series of novel 6-O-α- and -β-3-amino-3-deoxy- and 2-amino-2-deoxy-D-hexopyranosyl and hexofuranosyl analogues of the gentamicins.The 13C n.m.r. properties of representative compounds are described and the rotamer populations about the C-4-O and C-6-O glycosidic bonds are discussed.
- Daniels, Peter J. L.,Luce, Charles E.,Mallams, Alan K.,Morton, James B.,Saluja, Surinderjit S.,at al.
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p. 2137 - 2150
(2007/10/02)
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- 3',4'-Episulfido kanamycin B compounds
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New routes are provided for the synthesis of 3',4'-dideoxykanamycin B which is effective in inhibiting kanamycin-resistant organisms from kanamycin B through new intermediate, of which a fundamental process comprises a new reaction of a 3',4'-epoxy derivative of amino- and hydroxyl-protected kanamycin B with a xanthate to form a corresponding 3',4'-dideoxy-3'-eno derivative followed by removal of the amino- and hydroxyl-protecting groups thereof and by hydrogenation of the resulting 3',4'-dideoxy-3'-eno-kanamycin B. A 3',4'-episulfide derivative corresponding to the 3',4'-epoxy derivative which is formed as second product in the reaction of 3',4'-epoxy derivative with xanthate is also used as intermediate for the preparation of 3',4'-dideoxykanamycin B.
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- 1-N-(ω-aminoalkanesulfonyl) derivative of aminoglycosidic antibiotic and process for preparation thereof
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A new 1-N-(ω-aminoalkanesulfonyl) derivative of an aminoglycosidic antibiotic such as ribostamycin, 3'-deoxy- or 3',4'-dideoxy-ribostamycin, kanamycin A or B, and 3'-deoxy- or 3',4'-dideoxy-kanamycin B exhibits a broader, antibacterial spectrum than the parent aminoglycosidic antibiotic and is useful in the therapeutic treatment of infections caused by gram-positive and gram-negative bacteria including drug-resistant strains thereof. The aforesaid derivative may be made by reaction between the parent antibiotic and an amino-protected ω-aminoalkanesulfonic acid halide and removal of the amino-protecting group from the condensation product.
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- Selective acylation of the C-1 amino group of aminoglycoside antibiotics
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A novel process for preparing novel 1-N-acyl-4,6-di-(aminoglycosyl)aminocyclitols is disclosed. The compounds are useful as antibacterial agents.
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- A synthesis of 3',4'-dideoxykanamycin B.
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3',4',-Dideoxykanamycin B, the kanamycin B derivative that is active against resistant bacteria, was prepared from kanamycin B via N-tosylation, 3',4'-O-sulphonylation, 3',4'-unsaturation, and hydrogenation. The unsaturated intermediate was obtained from the 3',4'-di-O-sulphonyl derivatives by the action of sodium iodide in N,N-dimethylformamide; if zinc dust was added in this reaction, aziridine derivatives were formed. Removal of the tosyl group was successfully performed by using sodium in ammonia-ethylamine.
- Miyake,Tsuchiya,Umezawa,Umezawa
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p. 141 - 151
(2007/10/05)
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