Azathramycin CAS#: 76801-85-9; ChemWhat Code: 1137753
Identification
| Product Name | Azathramycin |
| IUPAC Name | (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one |
| Molecular Structure |  |
| CAS Registry Number | 76801-85-9 |
| EINECS Number | No data available |
| MDL Number | MFCD09038719 |
| Beilstein Registry Number | No data available |
| Synonyms | 9-Deoxo-9a-aza-9a-homoerythromycin AN’-desmethylazithromycin9a-N-desmethyl azithromycin |
| Molecular Formula | C37H70N2O12 |
| Molecular Weight | 734.958 |
| InChI | InChI=1S/C37H70N2O12/c1-14-26-37(10,45)30(41)23(6)38-18-19(2)16-35(8,44)32(51-34-28(40)25(39(11)12)15-20(3)47-34)21(4)29(22(5)33(43)49-26)50-27-17-36(9,46-13)31(42)24(7)48-27/h19-32,34,38,40-42,44-45H,14-18H2,1-13H3/t19-,20-,21+,22-,23-,24+,25+,26-,27+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1 |
| InChI Key | HRKNNHYKWGYTEN-HOQMJRDDSA-N |
| Canonical SMILES | CC[C@@H]1[C@@]([C@@H]([C@H](NC[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| CN106478541 | Macrolide derivative and application thereof | 2017 |
| US2004/14685 | Compounds, compositions and methods for treatment of inflammatory diseases and conditions | 2004 |
Physical Data
| Appearance | White to almost white powder |
| Solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
| Melting Point, °C | Solvent (Melting Point) |
| 125 – 128 | |
| 114 – 116 | |
| 115 | dichloromethane, methanol |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | 400 | |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | 101 | |
| TOCSY (Total Correlation Spectroscopy), Spectrum | 1H | 26.84 | ||
| Chemical shifts | 1H | chloroform-d1 | 20-25 | 500 |
| Chemical shifts | 13C | chloroform-d1 | 20-25 |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) |
| Bands | film |
| Description (Mass Spectrometry) | Comment (Mass Spectrometry) |
| spectrum | |
| ESI (Electrospray ionisation), LCMS (Liquid chromatography mass spectrometry), Spectrum | |
| HRMS (High resolution mass spectrometry), ESI (Electrospray ionisation), Spectrum | |
| Molecular peak |
Route of Synthesis (ROS)
| Conditions | Yield |
| With potassium borohydride In methanol at 0 – 5℃; for 2h; | 93% |
| Stage #1: 9-deoxo-6-deoxy-6,9-epoxy-9,9a-didehydro-9a-aza-homoerythromycin A With hydrogen; acetic acid; platinum(IV) oxide In methanol at 40 – 45℃; pH=5 – 6; Stage #2: With sodium hydroxide In water pH=11 – 12; | 85% |
| Stage #1: 9-deoxo-6-deoxy-6,9-epoxy-9,9a-didehydro-9a-aza-homoerythromycin A With sodium tetrahydroborate; acetic acid pH=6 – 8; Heating; Stage #2: With gluconic acid at 8℃; Reagent/catalyst; Temperature; | 84.4% |
| With sodium tetrahydroborate In methanol at 0 – 25℃; Inert atmosphere; | 77% |
| With methanol; sodium tetrahydroborate at 0 – 20℃; for 24h; | 70.3% |
Safety and Hazards
| GHS Hazard Statements | Not Classified |
Other Data
| Transportation | Under the room temperature and away from light |
| HS Code | No data available |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 734.969 |
| logP | 2.078 |
| HBA | 14 |
| HBD | 6 |
| Matching Lipinski Rules | 1 |
| Veber rules component | |
| Polar Surface Area (PSA) | 188.87 |
| Rotatable Bond (RotB) | 7 |
| Matching Veber Rules | 1 |
| Use Pattern |
| Azathramycin CAS#: 76801-85-9 intermediate in the preparation of Azithromycin dihydrate |
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Approved Manufacturers | |
| Caming Pharmaceutical Ltd | http://www.caming.com/ |
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Other Suppliers | |
| Watson International Limited | Visit Watson Official Website |
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