| Identification | More | [Name]
(2R,3S,4R,5S,8R,10R,11R,12S,13S,14R)-13-[(2,6-dideoxy-3-Cmethyl-3-O-methyl-a-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-7-propyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-b-D-xylo-hexopyranosyl]oxy]-1-oxa-7-azacyclopentadecan-15-one | [CAS]
145435-72-9 | [Synonyms]
GAMITHROMYCIN
(2R,3S,4R,5S,8R,10R,11R,12S,13S,14R)-13-[(2,6-dideoxy-3-Cmethyl-3-O-methyl-a-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-7-propyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-b-D-xylo-hexopyranosyl]oxy]-1-oxa-7-azacyclopentadecan-15-one | [EINECS(EC#)]
604-472-4 | [Molecular Formula]
C40H76N2O12 | [MDL Number]
MFCD09954125 | [MOL File]
145435-72-9.mol | [Molecular Weight]
777.04 |
| Questions And Answer | Back Directory | [Preparation]
To synthesize Gamithromycin from 9-deoxy-8a-aza-8a-homoerythromycin A as a precursor: Using dichloromethane as the reaction solvent, 9-deoxy-8a-aza-8a-homoerythromycin A undergoes an SN2 substitution reaction with bromopropane to obtain the final product Gamithromycin, with yields and contents of 66.1% and 63.87%, respectively. Alternatively, Gamithromycin can be synthesized using a propionaldehyde-cyanoborohydride hydrogenation method, with 9-deoxy-8α-aza-8α-homoerythromycin A as an intermediate, with a yield of 38.1%. Another method involves high-pressure hydrogenation using erythromycin 9,12-imine ether as a raw material and 5% Pt/C as a catalyst. Acetic acid is added, followed by the addition of propionaldehyde and acetic acid to obtain the target product Gamithromycin, with yields and purities of 79.0% and 88.9%, respectively. |
| Chemical Properties | Back Directory | [Melting point ]
>118°C (dec.) | [Boiling point ]
833.0±65.0 °C(Predicted) | [density ]
1.16±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
13.42±0.70(Predicted) | [color ]
White to Pale Yellow | [Stability:]
Hygroscopic | [InChIKey]
VWAMTBXLZPEDQO-DYFBWCQINA-N | [CAS DataBase Reference]
145435-72-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White to Off-White Solid | [Uses]
A macrolide compound which is known to have antibacterial activity, and is useful in the therapy of bacterial infections in mammals. Antibiotic. | [Uses]
Gamithromycin is a semi-synthetic macrocyclic lactone belonging to the azalide class derived from erthyromycin, typified by azithromycin. The synthesis of gamithromycin involves a ring expansion using a Beckmann rearrangement to produce the 15-membered dibasic macrolide. Gamithromycin provides a broader spectrum of action, higher acid stability and improved bioavailability compared to older analogues of the erythromycin class and has been exclusively developed for animal health applications. |
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J & K SCIENTIFIC LTD.
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18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
T&W GROUP
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021-61551611 13296011611 |
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www.trustwe.com/ |
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