Clarithromycin 9-Oxime

Base Information

• Chemical Name: Clarithromycin 9-Oxime
• CAS No.: 103450-87-9
• Molecular Formula: C38H70N2O13
• Molecular Weight: 762.979
• DSSTox Substance ID: DTXSID20433331
• Nikkaji Number: J2.066.161E
• ChEMBL ID: CHEMBL4277273
• Mol file: 103450-87-9.mol

Synonyms:Clarithromycin 9-Oxime;103450-87-9;(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-10-hydroxyimino-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one;127253-06-9;Clarithromycin E-9-Oxime;CHEMBL4277273;DTXSID20433331;6-O-Methylerythromycin [(E)-oxime]

Chemical Property of Clarithromycin 9-Oxime

Chemical Property:

• Melting Point: 169-171 °C
• Boiling Point: 827.7±65.0 °C(Predicted)
• PKA: 11.94±0.70(Predicted)
• PSA: 198.43000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 2.70080
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 8
• Exact Mass: 762.48779029
• Heavy Atom Count: 53
• Complexity: 1230

Purity/Quality:

99.90% ^*data from raw suppliers

Clarithromycin 9-oxime ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C(C(C(=NO)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)OC)C)C)O)(C)O
• Isomeric SMILES: CC[C@@H]1[C@@]([C@@H]([C@H](/C(=N/O)/[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)OC)C)C)O)(C)O
• Uses: Clarithromycin 9-Oxime is an impurity of Clarithromycin (C559750), a macrolide antibiotic.

Technology Process of Clarithromycin 9-Oxime

There total 7 articles about Clarithromycin 9-Oxime 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: 90.0%

clarithromycin (81103-11-9) → 3-O-descladinosyl-9-oxime clarithromycin (103450-87-9)

Guidance literature:

clarithromycin; With hydroxylamine hydrochloride; sodium acetate; In methanol; at 75 ℃; for 12h;

With hydrogenchloride; In methanol; water; at 75 ℃; for 5h;

DOI:10.1016/j.bmcl.2018.09.012

Reference yield:

2'-O,3'-N-bis(benzyloxycarbonyl)-N-demethylerythromycin A (81103-09-5) → clarithromycin 9-oxime (103450-87-9,127253-05-8,127253-06-9)

Guidance literature:

Multi-step reaction with 6 steps

1: NH₂OH*HCl, AcONa / methanol

2: CHCl₃ / isomerization

3: 82 percent / NaH / dimethylformamide

4: 76 percent / KOH / dimethylsulfoxide; tetrahydrofuran

5: H₂ / catalytic hydrogenation

6: HCOOH / ethanol / Heating

With potassium hydroxide; formic acid; hydroxylamine hydrochloride; hydrogen; sodium acetate; sodium hydride; In tetrahydrofuran; methanol; ethanol; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.3987/COM-90-5616

Reference yield:

C60H86N2O17 (101670-80-8,101757-72-6,103530-45-6) → clarithromycin 9-oxime (103450-87-9,127253-05-8,127253-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / catalytic hydrogenation

2: HCOOH / ethanol / Heating

With formic acid; hydrogen; In ethanol;

DOI:10.3987/COM-90-5616

upstream raw materials:

clarithromycin

formaldehyd

6-O-methyl-N-demethylerythromycin A 9-oxime

C₆₀H₈₆N₂O₁₇

Refernces

• 1、 Qin, Yinhui,Qiang, Shengsheng,Ji, Shengli,Liu, Zhiyang,Hu, Chaoyu,Ma, Shutao. "Synthesis and antibacterial activity of novel 3-O-arylalkylcarbamoyl-3-O-descladinosyl-9-O-(2-chlorobenzyl)oxime clarithromycin derivatives". . p. 3324 - 3328. Retrieved 2018.
• 2、 Watanabe, Yoshiaki,Adachi, Takashi,Asaka, Toshifumi,Kashimura, Masato,Morimoto, Shigeo. "CHEMICAL MODIFICATION OF ERYTHROMYCINS. VIII. A NEW EFFECTIVE ROUTE TO CLARITHROMYCIN (6-O-METHYLERYTHROMYCIN A)". . p. 2121 - 2124. Retrieved 2007/10/02.