Erythromycin, anhydro-, N-oxide

Base Information

• Chemical Name: Erythromycin, anhydro-, N-oxide
• CAS No.: 992-65-4
• Molecular Formula: C37H67NO14
• Molecular Weight: 749.937
• UNII: T9KL5GX5WQ
• DSSTox Substance ID: DTXSID50213784
• Nikkaji Number: J428.533F
• Wikidata: Q83089377
• Mol file: 992-65-4.mol

Synonyms:Erythromycin A N-oxide;Erythromycin, anhydro-, N-oxide;992-65-4;T9KL5GX5WQ;(2S,3R,4S,6R)-2-[[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-3-hydroxy-N,N,6-trimethyloxan-4-amine oxide;63950-90-3;Anhydroerythromycin-N-oxide;Erythromycin, N-oxide;USAF EL-99;UNII-T9KL5GX5WQ;SCHEMBL14342543;DTXSID50213784;LUIPOVCSQJTWHA-RWJQBGPGSA-N;ERYTHROMYCIN A 3''-N-OXIDE;ERYTHROMYCIN IMPURITY H [EP IMPURITY]

Chemical Property of Erythromycin, anhydro-, N-oxide

Chemical Property:

• PKA: 12.50±0.60(Predicted)
• PSA: 220.10000
• LogP: 1.81910
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 7
• Exact Mass: 749.45615581
• Heavy Atom Count: 52
• Complexity: 1220

Purity/Quality:

98% ^*data from raw suppliers

ErythromycinAN-oxide ^*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(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)[N+](C)(C)[O-])O)(C)O)C)C)O)(C)O
• Isomeric SMILES: CC[C@@H]1[C@@]([C@@H]([C@H](C(=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-])O)(C)O)C)C)O)(C)O
• Uses: Erythromycin A N-oxide is a minor analogue of the erythromycin complex isolated from Saccharopolyspora erythraea. The N-oxide is a facile metabolite formed in vivo which can revert to erythromycin A under reducing conditions. Despite its synthetic preparation in the 1950s, the biological activity of erythromycin A N-oxide has not been extensively studied. Erythromycin A N-oxide is a facile metabolite of erythromycin A.

Technology Process of Erythromycin, anhydro-, N-oxide

There total 17 articles about Erythromycin, anhydro-, N-oxide 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: 98.0%

erythromycin (114-07-8) → erythromycin A N-oxide (992-65-4)

Guidance literature:

With dihydrogen peroxide; In methanol; water; at 15 - 20 ℃; for 20h;

Reference yield: 58.0%

(9S)-9-dihydroerythromycin A N-oxide (138505-44-9) → erythromycin A N-oxide (992-65-4)

Guidance literature:

With bromine; bis(tri-n-butyltin)oxide; In dichloromethane; at 25 ℃; for 24h;

DOI:10.1016/0040-4039(91)80777-4

Reference yield:

9S-Dihydroerythronolide A aglycon (15562-19-3,28316-68-9) → erythromycin A N-oxide (992-65-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 87 percent / DL-10-camphorsulfonic acid / CH₂Cl₂ / 72 h / -30 °C

2: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.5 h / 25 °C

3: 95 percent / H₂ / Pd(OH)2/C / ethyl acetate / 2 h / 25 °C

4: 63 percent / silver triflate, 4A molecular sieves / CH₂Cl₂; toluene / 4 h / 25 °C

5: 100 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.25 h / 25 °C

6: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH₂Cl₂ / 0.17 h / -35 °C

7: 66 percent / 50percent aq. AcOH / 12 h / 40 °C

8: 54 percent / H₂ / Raney Ni (W₄) / ethanol / 1.5 h / 40 °C

9: 99 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.17 h / 25 °C

10: 58 percent / bis(tri-n-butyltin) oxide, Br₂ / CH₂Cl₂ / 24 h / 25 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; bromine; silver trifluoromethanesulfonate; pyridinium p-toluenesulfonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; bis(tri-n-butyltin)oxide; palladium dihydroxide; Raney Ni (W₄); In ethanol; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/ja00118a008

upstream raw materials:

erythromycin

(9S)-9-dihydroerythromycin A N-oxide

N-Demethylerythromycin A

9S-Dihydroerythronolide A aglycon

Downstream raw materials:

6-O-methylerythromycin A N-oxide

erythromycin

Refernces

• 1、 -. "PREPARATION AND UTILITY OF SUBSTITUTED ERYTHROMYCIN ANALOGS". Page/Page column 28; 31. . Retrieved 2008/06/13.
• 2、 Paesen, Jos,Roets, Eugene,Janssen, Gerard,Busson, Roger,Cachet, Thierry,Hoogmartens, Jos. "SYNTHESIS OF ERYTHROMYCIN RELATED MACROLIDES". . p. 205 - 212. Retrieved 2007/10/03.