N'-(Desmethyl)azithromycin

Base Information

• Chemical Name: N'-(Desmethyl)azithromycin
• CAS No.: 172617-84-4
• Molecular Formula: C37H70N2O12
• Molecular Weight: 734.969
• UNII: 3E93A68ETO
• DSSTox Substance ID: DTXSID30169356
• Nikkaji Number: J398.493A
• Wikidata: Q27257112
• ChEMBL ID: CHEMBL2022716
• Mol file: 172617-84-4.mol

Synonyms:N'-(Desmethyl)azithromycin;172617-84-4;N-Demethylazithromycin;3'-N-Demethylazithromycin;CP-64434;UNII-3E93A68ETO;Azithromycin impurity I [EP];3E93A68ETO;CP 64434;3'-N-Desmethylazithromycin;N-Desmethyl Azithromycin (Impurity I);(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-11-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one;N/'-(Desmethyl)azithromycin;SCHEMBL9969023;CHEMBL2022716;DTXSID30169356;FZYUKBLYECHAGN-HOQMJRDDSA-N;N-DEMETHYLAZITHROMYCIN [USP-RS];AZITHROMYCIN IMPURITY I [EP IMPURITY];A899421;J-010836;Q27257112;(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10- trihydroxy-13-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6- dimethyltetrahydro-2H-pyran-2-yl)oxy)-11-(((2R,3R,4S,6R)- 3-hydroxy-6-methyl-4-(methylamino)tetrahydro-2H-pyran-2- yl)oxy)-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan- 15-one

Chemical Property of N'-(Desmethyl)azithromycin

Chemical Property:

• Boiling Point: 821.4±65.0 °C(Predicted)
• PKA: 13.28±0.70(Predicted)
• PSA: 188.87000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 1.88730
• Storage Temp.: room temp
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 7
• Exact Mass: 734.49287567
• Heavy Atom Count: 51
• Complexity: 1120

Purity/Quality:

97% ^*data from raw suppliers

N’-DesmethylAzithromycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C(C(N(CC(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)NC)O)(C)O)C)C)C)O)(C)O
• Isomeric SMILES: CC[C@@H]1[C@@]([C@@H]([C@H](N(C[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)NC)O)(C)O)C)C)C)O)(C)O
• Uses: N’-Desmethyl Azithromycin (Azithromycin EP Impurity I) is a metabolite of Azithromycin (A927000) as potential anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agent. A metabolite of Azithromycin (A927000) as potential anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agent.

Technology Process of N'-(Desmethyl)azithromycin

There total 4 articles about N'-(Desmethyl)azithromycin 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: 77.9%

Zithromax(R) (83905-01-5,92470-27-4) → (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)‐2‐ethyl‐3,4,10‐trihydroxy‐13‐{(2R,4R,5S,6S)‐5‐hydroxy‐4‐methoxy‐4,6‐dimethyl-tetrahydropyran‐2‐yloxy}‐11‐{(2S,3R,4S,6R)‐3‐hydroxy‐6‐methyl‐4‐methylamino-tetrahydropyran‐2‐yloxy}‐3,5,6,8,10,12,14‐heptamethyl‐1‐oxa‐6‐azacyclopentadecan‐15‐one (172617-84-4)

Guidance literature:

Zithromax(R); With diethylazodicarboxylate; In acetone; toluene; at 20 ℃; for 25h;

With ammonium chloride; In methanol; for 1h; Reflux;

With ammonium hydroxide; In water; pH=9.4;

DOI:10.1016/j.ejmech.2012.01.039

Reference yield:

azithromycin-3'-N-oxide (90503-06-3) → (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)‐2‐ethyl‐3,4,10‐trihydroxy‐13‐{(2R,4R,5S,6S)‐5‐hydroxy‐4‐methoxy‐4,6‐dimethyl-tetrahydropyran‐2‐yloxy}‐11‐{(2S,3R,4S,6R)‐3‐hydroxy‐6‐methyl‐4‐methylamino-tetrahydropyran‐2‐yloxy}‐3,5,6,8,10,12,14‐heptamethyl‐1‐oxa‐6‐azacyclopentadecan‐15‐one (172617-84-4)

Guidance literature:

With sodium hydrogencarbonate; N-fluorobis(benzenesulfon)imide; In dichloromethane; at 30 ℃; for 24h; Solvent;

Reference yield:

2'-deoxy-3'-dedimethylamino-2',3'-epoxyazithromycin → (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)‐2‐ethyl‐3,4,10‐trihydroxy‐13‐{(2R,4R,5S,6S)‐5‐hydroxy‐4‐methoxy‐4,6‐dimethyl-tetrahydropyran‐2‐yloxy}‐11‐{(2S,3R,4S,6R)‐3‐hydroxy‐6‐methyl‐4‐methylamino-tetrahydropyran‐2‐yloxy}‐3,5,6,8,10,12,14‐heptamethyl‐1‐oxa‐6‐azacyclopentadecan‐15‐one (172617-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1: isopropyl alcohol / 80 °C

2: sodium hydrogencarbonate; potassium carbonate; iodine / methanol; water / 20 °C

With iodine; sodium hydrogencarbonate; potassium carbonate; In methanol; water; isopropyl alcohol;

upstream raw materials:

Zithromax(R)

azithromycin-3'-N-oxide

Downstream raw materials:

C₄₁H₇₄N₂O₁₂

C₅₃H₉₁N₃O₁₅

(3'-N-(4-ethynylbenzyl))azithromycin

2'-O,3'-N-(carbonimidoyl)-3'-N-demethyl-N'-[4-(metoxy)phenyl]-9a-methyl-9a-aza-9a-homoerythromycin A