Rokitamycin

Take Kitasamycin as raw material. 10g kitasamycin A5 was dissolved in 50ml dry 1, 2-dichloroethane and 4.2ml acetic anhydride, and stirred at room temperature for 0.5h. The reaction solution was added to 200ml ice water, adjusted to Ph=10 with 7% ammonia water, and then extracted with 50ml 1, 2-dichloroethane. The extract was dried with anhydrous sodium sulfate and concentrated under reduced pressure. 10g of crude 2'-O-acetylguitaromycin A5(I) with a yield of 94.8%. 10g of 2'-O-acetylkitatamycin A5(I) was dissolved in 50ml of dry dichloroethane, 10g of tribenzylamine and 6.6ml of trimethylchlorosilane were added, and the mixture was stirred at 5-10°C for 15h. Then the reaction solution was poured into 200rnl of water, adjusted to Ph=9.5 with 7% ammonia, and extracted with 1, 2-dichloroethane. After the extract was washed with water, it was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 12.7 g of crude 2'-O-acetyl-3, 9-di-O-trimethylsililakinamycin A5(II) with a yield of 96.1%. The crude product of the above (II) was dissolved in 50ml of dry 1, 2-dichloroethane, 31g of tribenzylamine was added, and 11.25ml of propionyl chloride was added dropwise under cooling and stirring in an ice bath, and stirred at 75°C for 20h. The reaction solution was poured into 200 ml of water, adjusted to a Ph value of 9.5 with ammonia, and then extracted with 100 ml of 1, 2-dichloroethane. After the extract was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to obtain 2'-O-acetyl-17, 18-enol-18, 3''-di-O-propionyl-3, 9-di- O-trimethylsilicatamycin A5 (Ⅲ) and a small amount of 2'-O-acetyl-3”-O-propionyl-3, 9-di-O-trimethylsilicatiromycin A5(Ⅳ) ) And a large amount of tribenzylamine. Without separation, add 495ml methanol and 55ml 8% potassium carbonate aqueous solution and stir at room temperature for 1h to obtain 2'-O-acetyl-3”-O-propionyl-kitasamycin A5 (V) solution. Adjust to Ph=7.5 with acetic acid, reflux for 20h, and then concentrate under reduced pressure. The residue was dissolved in 1, 2-dichloroethane, washed with 3% ammonia water once, then washed twice with water, and then concentrated under reduced pressure. The residue was dissolved in cold methanol and filtered to remove insoluble tribenzylamine. The filtrate was concentrated under reduced pressure to obtain 10.4 g of crude rotamycin with a yield of 94.7%. The crude product was dissolved in a small amount of benzene, and column chromatography was carried out on silica gel (1.5crn×60cm). The eluent was benzene-ethyl acetate-methanol (36:4:1, volume ratio). Collect the components near Rf=0.57 Part of the eluates are combined and evaporated to dryness under reduced pressure to obtain 7.5 g of pure rotamycin with a melting point of about 116°C. The total yield is 70%.

Macrolide antibiotics have strong anti-Cui activity against Gram-positive bacteria, anaerobic bacteria and Mycoplasma. Used for various infections caused by sensitive bacteria, such as pneumonia, mycoplasma pneumonia, otitis media, equine inflammation, periodontitis, paranasal sinusitis, subcutaneous abscess, sweat gland inflammation, laryngitis, acute bronchitis, tonsillitis boil, Erysipelas, etc.

Molecular Weight:828.0
XLogP3:3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:16
Rotatable Bond Count:15
Exact Mass:827.46672049
Monoisotopic Mass:827.46672049
Topological Polar Surface Area:206
Heavy Atom Count:58
Complexity:1380
Undefined Atom Stereocenter Count:16
Undefined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes