Clarithromycin oxime

Base Information

• Chemical Name: Clarithromycin oxime
• CAS No.: 127253-06-9
• Molecular Formula: C38H70N2O13
• Molecular Weight: 762.979
• UNII: MB5LXB6ZMM
• Nikkaji Number: J291.603G,J2.066.163A
• Wikidata: Q82247458
• Mol file: 127253-06-9.mol

Synonyms:Clarithromycin oxime;Clarithromycin E-9-Oxime;Clarithromycin Impurity C;127253-06-9;MB5LXB6ZMM;SCHEMBL12859862;MWBJRTBANFUBOX-SQYJNGITSA-N;6-0-methylerythromycin A 9-oxime;9(E)-6-O-Methyl-erythromycin oxime;6-O-Methylerythromycin A (E)-9-oxime;Erythromycin, 6-O-methyl-, 9-oxime, (9E)-;(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R,E)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-10-(hydroxyimino)-7-methoxy-

Chemical Property of Clarithromycin oxime

Chemical Property:

• Boiling Point: 827.7±65.0 °C(Predicted)
• PKA: 11.94±0.70(Predicted)
• PSA: 198.43000
• Density: 1.26
• 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% ^*data from raw suppliers

ClarithromycinE-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 (Clarithromycin EP Impurity C) is an impurity of Clarithromycin (C559750), a macrolide antibiotic.

Technology Process of Clarithromycin oxime

There total 10 articles about Clarithromycin 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) → 6-methoxyerythromycin A 9-oxime (127253-06-9)

Guidance literature:

With hydroxylamine hydrochloride; sodium acetate; at 80 ℃;

DOI:10.1016/j.ejmech.2013.08.023

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:

formaldehyd

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

C₆₀H₈₆N₂O₁₇

C₅₉H₈₄N₂O₁₇

Downstream raw materials:

6-O-Me Ery A 9(Z)-oxime

C₄₅H₇₈N₂O₁₂

C₄₆H₇₉N₃O₁₃

3'-N-demethyl-4-O-(2-diethylaminoethanoyl)-2'-O-3'-N-di-{[(phenylmethyl)oxy]carbonyl}-6-O-methyl-9a-aza-9a-homoerythromycin A

Refernces

• 1、 -. "SUBSTANTIALLY PURE CLARITHROMYCIN 9-OXIME AND ITS PREPARATION THEREOF". Page/Page column 9-10. . Retrieved 2021/05/07.
• 2、 -. "PROCESS FOR THE PREPARATION OF 6-O-METHYLERYTHROMYCIN A 9-OXIME". Page/Page column 6. . Retrieved 2009/03/07.