(4E)-10alpha-[3alpha-Acetoxy-4beta-(dimethylamino)-6beta-methyltetrahydro-2H-pyran-2beta-yloxy]-3-[(1H-imidazole-1-yl)carbonyloxy]-9-methoxy-2alpha-ethyl-3alpha,5,7alpha,9alpha,11beta,13beta-hexamethyl-1-oxacyclotetradecane-4-ene-6,12,14-trione

Base Information

• Chemical Name: (4E)-10alpha-[3alpha-Acetoxy-4beta-(dimethylamino)-6beta-methyltetrahydro-2H-pyran-2beta-yloxy]-3-[(1H-imidazole-1-yl)carbonyloxy]-9-methoxy-2alpha-ethyl-3alpha,5,7alpha,9alpha,11beta,13beta-hexamethyl-1-oxacyclotetradecane-4-ene-6,12,14-trione
• CAS No.: 160145-83-5
• Molecular Formula: C11H14ClNO
• Molecular Weight: 705.846
• DSSTox Substance ID: DTXSID101099263
• Nikkaji Number: J2.452.721B
• ChEMBL ID: CHEMBL320375
• Mol file: 160145-83-5.mol

Synonyms:CHEMBL320375;SCHEMBL14270528;DTXSID101099263;(4E)-10alpha-[3alpha-Acetoxy-4beta-(dimethylamino)-6beta-methyltetrahydro-2H-pyran-2beta-yloxy]-3-[(1H-imidazole-1-yl)carbonyloxy]-9-methoxy-2alpha-ethyl-3alpha,5,7alpha,9alpha,11beta,13beta-hexamethyl-1-oxacyclotetradecane-4-ene-6,12,14-trione;Erythromycin, 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy]-10,11-didehydro-11-deoxy-6-O-methyl-3-oxo-, 2'-acetate 12-(1H-imidazole-1-carboxylate)

Chemical Property of (4E)-10alpha-[3alpha-Acetoxy-4beta-(dimethylamino)-6beta-methyltetrahydro-2H-pyran-2beta-yloxy]-3-[(1H-imidazole-1-yl)carbonyloxy]-9-methoxy-2alpha-ethyl-3alpha,5,7alpha,9alpha,11beta,13beta-hexamethyl-1-oxacyclotetradecane-4-ene-6,12,14-trione

Chemical Property:

• Melting Point: 152 °C
• Boiling Point: 352.1 °C at 760 mmHg
• PKA: 10.72±0.70(Predicted)
• Flash Point: 166.7 °C
• PSA: 161.79000
• Density: 1.15 g/cm³
• LogP: 5.42580
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 9
• Exact Mass: 705.38365958
• Heavy Atom Count: 50
• Complexity: 1290

Purity/Quality:

99% ^*data from raw suppliers

TELITHROMYCIN INTERMEDIATE-(7A) 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C=C(C(=O)C(CC(C(C(C(=O)C(C(=O)O1)C)C)OC2C(C(CC(O2)C)N(C)C)OC(=O)C)(C)OC)C)C)(C)OC(=O)N3C=CN=C3
• Isomeric SMILES: CC[C@@H]1[C@@](/C=C(/C(=O)[C@@H](C[C@@]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O[C@H]2[C@@H]([C@H](C[C@H](O2)C)N(C)C)OC(=O)C)(C)OC)C)\C)(C)OC(=O)N3C=CN=C3

Technology Process of (4E)-10alpha-[3alpha-Acetoxy-4beta-(dimethylamino)-6beta-methyltetrahydro-2H-pyran-2beta-yloxy]-3-[(1H-imidazole-1-yl)carbonyloxy]-9-methoxy-2alpha-ethyl-3alpha,5,7alpha,9alpha,11beta,13beta-hexamethyl-1-oxacyclotetradecane-4-ene-6,12,14-trione

There total 9 articles about (4E)-10alpha-[3alpha-Acetoxy-4beta-(dimethylamino)-6beta-methyltetrahydro-2H-pyran-2beta-yloxy]-3-[(1H-imidazole-1-yl)carbonyloxy]-9-methoxy-2alpha-ethyl-3alpha,5,7alpha,9alpha,11beta,13beta-hexamethyl-1-oxacyclotetradecane-4-ene-6,12,14-trione 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: 97.0%

1,1'-carbonyldiimidazole (530-62-1) + 2'-O-acetyl-10,11-didehydro-11-deoxy-3-O-descladinosyl-3-oxo-6-O-methyl-erythromycin A (214694-76-5) → 2'-O-acetyl-10,11-didehydro-11-deoxy-12-O-(1H-1-imidazoylcarbonyl)-3-O-descladinosyl-3-oxo-6-O-methyl-erythromycin A (160145-83-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 25 ℃; for 1h;

DOI:10.1021/acs.joc.1c02799

Reference yield:

clarithromycin (81103-11-9) → 2'-O-acetyl-10,11-didehydro-11-deoxy-12-O-(1H-1-imidazoylcarbonyl)-3-O-descladinosyl-3-oxo-6-O-methyl-erythromycin A (160145-83-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / aq. HCl / 2 h / Ambient temperature

2: 82 percent / K₂CO₃ / acetone / 20 h / Ambient temperature

3: EDC*HCl, pyridinium trifluoroacetate, DMSO / CH₂Cl₂ / 4 h / Ambient temperature

4: 79 percent / pyridine / 5 h / Ambient temperature

5: 88 percent / DBU / acetone / 20 h / Ambient temperature

6: 1.) NaH / 1.) DMF, -10 deg C, 2.) DMF, -10 deg C, 1 h

With pyridine; hydrogenchloride; pyridinium trifluroacetate; sodium hydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; acetone;

DOI:10.1021/jm980240d

Reference yield:

3-O-descladinosylclarithromycin (118058-74-5) → 2'-O-acetyl-10,11-didehydro-11-deoxy-12-O-(1H-1-imidazoylcarbonyl)-3-O-descladinosyl-3-oxo-6-O-methyl-erythromycin A (160145-83-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / K₂CO₃ / acetone / 20 h / Ambient temperature

2: EDC*HCl, pyridinium trifluoroacetate, DMSO / CH₂Cl₂ / 4 h / Ambient temperature

3: 79 percent / pyridine / 5 h / Ambient temperature

4: 88 percent / DBU / acetone / 20 h / Ambient temperature

5: 1.) NaH / 1.) DMF, -10 deg C, 2.) DMF, -10 deg C, 1 h

With pyridine; pyridinium trifluroacetate; sodium hydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; acetone;

DOI:10.1021/jm980240d

upstream raw materials:

1,1'-carbonyldiimidazole

2'-O-acetyl-10,11-didehydro-11-deoxy-3-O-descladinosyl-3-oxo-6-O-methyl-erythromycin A

clarithromycin

3-O-descladinosylclarithromycin

Downstream raw materials:

telithromycin

(3aS,4R,7R,9R,10R,11R,13R,15aR)-10-((2S,3R,4S,6R)-4-Dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-(4-phenyl-butyl)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Refernces

• 1、 Xu, Peng,Liu, Lu,Chen, Xiao-zhuo,Li, Yun,Liu, Jian,Jin, Zhi-ping,Wang, Guang-qiang,Lei, Ping-sheng. "Synthesis of novel macrolide derivatives with imidazo[4,5-b]pyridinyl sulfur contained alkyl side chains and their antibacterial activity". supporting information; experimental part. p. 4079 - 4083. Retrieved 2010/04/24.
• 2、 Agouridas, Constantin,Denis, Alexis,Auger, Jean-Michel,Benedetti, Yannick,Bonnefoy, Alain,Bretin, Fran?ois,Chantot, Jean-Fran?ois,Dussarat, Arlette,Fromentin, Claude,D'Ambrières, Solange Gouin,Lachaud, Sylvette,Laurin, Patrick,Martret, Odile Le,Loyau, Véronique,Tessot, Nicole. "Synthesis and antibacterial activity of ketolides (6-O-methyl-3- oxoerythromycin derivatives): A new class of antibacterials highly potent against macrolide-resistant and -susceptible respiratory pathogens". . p. 4080 - 4100. Retrieved 2007/10/03.