21238-30-2

Usage

Uses

Used in Pharmaceutical Industry:
9-Deoxy-9-oxoleucomycin V 3-acetate 4''-O-(3-methylbutanoate) is used as an intermediate in the synthesis of Carbomycin, a macrolide antibiotic complex. It contributes to the development of this antibiotic, which is effective against a wide range of bacterial infections due to its ability to inhibit bacterial protein synthesis.
Used in Antibacterial Applications:
As a component in the synthesis of Carbomycin, 9-Deoxy-9-oxoleucomycin V 3-acetate 4''-O-(3-methylbutanoate) plays a role in the creation of an antibiotic that is used for treating various bacterial infections. Its broad-spectrum activity makes it a valuable asset in the fight against antibiotic-resistant bacteria.
Used in Research and Development:
9-Deoxy-9-oxoleucomycin V 3-acetate 4''-O-(3-methylbutanoate) is also utilized in research and development for the study of macrolide antibiotics and their potential applications in medicine. This includes exploring new methods of synthesis, understanding their mechanisms of action, and identifying ways to improve their efficacy and safety.

InChI:InChI=1/C42H67NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29,31,34-41,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1

Upstream product

• 16846-24-5 josamycin 

Downstream Products

• 676997-02-7 Acetic acid (2S,3R,4S,5S,6R)-2-[(11E,13E)-(4R,5S,6S,7R,9R,16R)-4-acetoxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxo-ethyl)-oxacyclohexadeca-11,13-dien-6-yloxy]-4-dimethylamino-6-methyl-5-phenylcarbamoyloxy-tetrahydro-pyran-3-yl ester 
• 676997-08-3 Acetic acid (2S,3R,4S,5S,6R)-2-[(11E,13E)-(4R,5S,6S,7R,9R,16R)-4-acetoxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxo-ethyl)-oxacyclohexadeca-11,13-dien-6-yloxy]-5-benzylcarbamoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester 
• 676997-11-8 Acetic acid (2S,3R,4S,5S,6R)-2-[(11E,13E)-(4R,5S,6S,7R,9R,16R)-4-acetoxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxo-ethyl)-oxacyclohexadeca-11,13-dien-6-yloxy]-4-dimethylamino-6-methyl-5-phenethylcarbamoyloxy-tetrahydro-pyran-3-yl ester 
• 676997-09-4 Acetic acid (2S,3R,4S,5S,6R)-2-[(11E,13E)-(4R,5S,6S,7R,9R,16R)-4-acetoxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxo-ethyl)-oxacyclohexadeca-11,13-dien-6-yloxy]-4-dimethylamino-5-(4-methoxy-benzylcarbamoyloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 676997-10-7 Acetic acid (2S,3R,4S,5S,6R)-2-[(11E,13E)-(4R,5S,6S,7R,9R,16R)-4-acetoxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxo-ethyl)-oxacyclohexadeca-11,13-dien-6-yloxy]-4-dimethylamino-6-methyl-5-(4-nitro-benzylcarbamoyloxy)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Characterization of a new component and impurities in josamycin by trap-free two-dimensional liquid chromatography coupled to ion trap time-of-flight mass spectrometry

Rationale: The toxicities of the impurities of a drug will affect the clinical effects and cause potential health risk; therefore, it is essential to study profiles of the impurities. In this study, a new structural type of component and two acid degradation impurities in josamycin were discovered and characterized for the further improvement of official monographs in pharmacopoeias. Methods: The component and acid degradation impurities in josamycin were separated and preliminary characterized by trap-free two-dimensional liquid chromatography coupled to high-resolution ion trap time-of-flight mass spectrometry (2D LC/IT-TOF MS) in both positive and negative electrospray ionization mode. The eluent of each peak from the first dimensional chromatographic system was trapped by a switching valve and subsequently transferred to the second dimensional chromatographic system, which was connected to the mass spectrometer. Full scan MS was firstly conducted to obtain the exact m/z values of the molecules. Then LC/MS/MS and LC/MS/MS/MS experiments were performed on the compounds of interest. Results: A new structural type of component, which was named as josamycin A, and two acid degradation impuritiess, which were identified as impurity I and impurity II, were discovered in josamycin. Their structures and fragmentation pattern were deduced according to MSn data. Furthermore, josamycin A was synthesized and impurity I was separated by preparative HPLC. The structures of josamycin A and the impurities were confirmed by 1H NMR and 13C NMR data. Conclusions: Josamycin A was produced when the hydroxyl group on the macrolide of josamycin was oxidized into a carbonyl group. Impurity I and impurity II were produced by the loss of one molecule of acetyl mycaminose from josamycin and josamycin A, respectively. Compared with josamycin, the experimental results showed that josamycin A had a higher antibacterial activity with similar cytotoxicity, while impurity I had no antibacterial activity but a higher cytotoxicity. As a result, the control of impurity I is significant.

Synthesis of novel 4′-substituted 16-membered ring macrolide antibiotics derived from leucomycins

A series of novel 4′-substituted 16-membered ring macrolides was synthesized by the cleavage of the mycarose sugar and subsequent modification of 4′-hydroxyl group. This new class of macrolides antibiotics is acid stable. The synthetic methodology described here is expected to find application in the synthesis of new generation of macrolides that target the emerging bacterial resistance.

Macrolide compounds

Compounds of general formula: STR1 in which: A denotes either an oxygen atom, or a group of the formula N O-Y-R5, , B, X, Y, R1, R2, R3, R4, R5, R8, R9 and R10 being defined in the description. Medicinal products containing the same, and their use in broad-spectrum antibiotic therapy for the treatment of infections.

Process for the conversion of niddamycin to leucomycin A1, leucomycin A3, carbomycin B and other antibiotics and related 3-O-esters

Covers the process for the conversion of niddamycin to known compounds such as carbomycin B, leucomycin A1 and A3, and other antibiotic compounds as well as novel 3-(O)-esters 3-(0)-esters and dimethyl acetal derivatives not obtained from natural sources. These compounds are represented by the general formula: SPC1 Wherein R is hydroxy or oxygen, R1 is hydrogen, HCO (formyl), CH3 CO (acetyl), CH3 CH2 CO (propionyl) or CH3 CH2 CH2 CO (butyryl); wherein R2 is hydrogen or equivalent to R1 and R3 is CHO or CH(OCH3)2. These compounds are useful antimicrobial agents.