(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
Arbekacin
CAS: 51025-85-5
Molecular Formula: C22H44N6O10
(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide - Names and Identifiers
(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide - Physico-chemical Properties
| Molecular Formula | C22H44N6O10 |
| Molar Mass | 552.62 |
| Density | 1.47±0.1 g/cm3(Predicted) |
| Boling Point | 904.0±65.0 °C(Predicted) |
| pKa | 13.07±0.70(Predicted) |
| Physical and Chemical Properties | Chemical properties abbekacin dicarbonate (Ajbekacin Dicarbonate):Q2H44N6O10?2H2CO3. Colorless crystalline powder, melting point 178 ℃ (decomposition). [α]{D24 86.8 °(C = 0.77, water). Acute toxicity LD50 mice (mg/kg):>150 intravenous injection. |
| Use | Use of kanamycin, gentamicin, amikacin resistant bacteria have strong antibacterial activity. For sensitive bacteria caused by sepsis, Pneumonia, etc. |
(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide - Upstream Downstream Industry
(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide - Production method
3,4 '-dideoxykanamycin B and equivalent tert-butoxycarbonyl azide, in a mixed solution of water, pyridine and triethylamine (10:10:1), at room temperature React for 18h. Then, 6 '-N-tert-butoxycarbonyl -3',4 '-dideoxykanamycin B was obtained by Amberlite CG50(NH4 +) column chromatography with 49% yield, melting point 136~140 ℃ (decomposition),[α] {d} 26+112 (C = 1.0, water). At the same time, the 36% unreacted 3 ',4'-dideoxykanamycin B was recovered.
6 '-N-tert-butoxycarbonyl -3',4 '-dideoxykanamycin B(1.1g,2.0 mmo1) and tert-butoxycarbonyl azide (320mg,2.2 mmo1) reacted under the same conditions as above to give 1.41g yellow powder. Without purification, dissolve in 20ml of water and 10ml of dimethoxyethane, acylate with (S)-4-tert-butoxyamino-2-hydroxybutyric acid (N-hydroxysuccinimide) ester (696mg,2.2 mmo1) in a solution of 10ml of dimethoxyethane at room temperature for 20h. React with 10ml 90% trifluoroacetic acid at room temperature for 40min to remove tert-butoxycarbonyl. The reaction solution is concentrated and the product is eluted with Amberlite CG50(NH4 +) column chromatography, eluted with water and 0.5mol/L ammonia water, and then eluted with 0.75mol/L ammonia water. 162mg abbekacin dicarbonate was obtained with 12% yield, melting point 178 ℃ (decomposition),[α]{d} 24+87 (c = 0.77, water).
Last Update：2024-04-10 22:29:15
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Tel: +86 0571-86722205
Email: sales@chinaskyrun.com
Mobile: +8618958170122
QQ: 2531159185
Wechat: chinaskyrun
Spot supply
Product Name: Arbekacin Visit Supplier Webpage Request for quotationCAS: 51025-85-5
Tel: 609-228-6898
Email: sales@medchemexpress.com
tech@medchemexpress.com
Mobile: 609-228-6898
View History
(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
Ethyl 4-Methyl-1H-indole-2-carboxylate
791786-33-9
213406-50-9
N1-(2-benzoyl-4-chlorophenyl)-3-(1,2,3,4-tetrahydroquinolin-1-yl)propanamide
270-53-1
hypobromous acid
Ethyl 4-Methyl-1H-indole-2-carboxylate
791786-33-9
213406-50-9
N1-(2-benzoyl-4-chlorophenyl)-3-(1,2,3,4-tetrahydroquinolin-1-yl)propanamide
270-53-1
hypobromous acid
Raw Materials for (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
Trifluoroacetic acid
1-Methylpyrazole-4-ethoxycarbonyl-5-ethoxycarbonylsulfonamide
Benzyl chloroformate
Hydrogen
Palladium hydroxide
1-Methylpyrazole-4-ethoxycarbonyl-5-ethoxycarbonylsulfonamide
Benzyl chloroformate
Hydrogen
Palladium hydroxide