Carbomycin B

Base Information

• Chemical Name: Carbomycin B
• CAS No.: 21238-30-2
• Molecular Formula: C₄₂H₆₇NO₁₅
• Molecular Weight: 825.992
• UNII: 5H7K5W89FA
• DSSTox Substance ID: DTXSID601024930
• Nikkaji Number: J39.580C
• Wikidata: Q27262180
• Mol file: 21238-30-2.mol

Synonyms:CARBOMYCIN B;21238-30-2;5H7K5W89FA;9-Deoxy-9-oxoleucomycin v 3-acetate 4b-(3-methylbutanoate);Leucomycin v, 9-deoxy-9-oxo-, 3-acetate 4b-(3-methylbutanoate);(2S,3S,4R,6S)-6-(((2R,3S,4R,5R,6S)-6-(((4R,5S,6S,7R,9R,11E,13E,16R)-4-acetoxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-6-yl)oxy)-4-(dimethylamino)-5-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4-hydroxy-2,4-dimethyltetrahydro-2H-pyran-3-yl 3-methylbutanoate;CARBOMYCIN B [MI];UNII-5H7K5W89FA;SCHEMBL3822906;DTXSID601024930;[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,11E,13E,16R)-4-acetyloxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate;Q27262180

Chemical Property of Carbomycin B

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 141-144° (dec)
• Boiling Point: 879.7°Cat760mmHg
• PKA: pKb 7.56(at 25℃)
• Flash Point: 485.8°C
• PSA: 202.89000
• Density: 1.2g/cm³
• LogP: 3.22160
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 14
• Exact Mass: 825.45107043
• Heavy Atom Count: 58
• Complexity: 1430

Purity/Quality:

98% ^*data from raw suppliers

MagnamycinB(>80%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC=CC=CC(=O)C(CC(C(C(C(CC(=O)O1)OC(=O)C)OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C
• Isomeric SMILES: C[C@@H]1C/C=C/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)OC(=O)C)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C
• Uses: Magnamycin B is an intermediate in the synthesis of Carbomycin (C176680), an macrolite antibiotic complex similar to Leucomycin and Erythromycin, produced by Stroptomyces halstedii.

Technology Process of Carbomycin B

There total 6 articles about Carbomycin B which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 46.0%

josamycin (16846-24-5) → Magnamycin-B (21238-30-2)

Guidance literature:

With pyridine; chromium(VI) oxide; at 20 ℃; for 3h;

DOI:10.1016/j.bmcl.2003.10.028

Reference yield: 36.4%

Josamycin base → Magnamycin-B (21238-30-2)

Guidance literature:

With sulfur trioxide; triethylamine; In dimethyl sulfoxide;

Reference yield:

→ Magnamycin-B (21238-30-2)

Guidance literature:

upstream raw materials:

josamycin

Downstream raw materials:

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

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

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

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

Refernces

• 1、 Liu, Guijun,Xu, Yu,Sang, Jing,Zhu, Bingqi,Wang, Jian. "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". . p. 1058 - 1066. Retrieved 2019.
• 2、 -. "Macrolide compounds". . . Retrieved 2008/06/13.