Desosaminylazithromycin

Base Information

• Chemical Name: Desosaminylazithromycin
• CAS No.: 117693-41-1
• Molecular Formula: C30H58N2O9
• Molecular Weight: 590.799
• Hs Code.: 2934990002
• UNII: E4730HW9T7
• Nikkaji Number: J398.494J
• ChEMBL ID: CHEMBL1645595
• Mol file: 117693-41-1.mol

Synonyms:Desosaminylazithromycin;Azithromycin Impurity J;Descladinose Azithromycin;13-o-Decladinosylazithromycin;117693-41-1;CP 66458;CP-66458;Azithromycin impurity J [EP];UNII-E4730HW9T7;E4730HW9T7;(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10,13-tetrahydroxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one;1-Oxa-6-azacyclopentadecan-15-one, 2-ethyl-3,4,10,13-tetrahydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-;1-Oxa-6-azacyclopentadecan-15-one, 2-ethyl-3,4,10,13-tetrahydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-, (2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*))-;Decladinosylazithromycin;descladinosyl azithromycin;Azithromycin EP Impurity J;CHEMBL1645595;SCHEMBL12966175;(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(DIMETHYLAMINO)-3-HYDROXY-6-METHYLOXAN-2-YL]OXY}-2-ETHYL-3,4,10,13-TETRAHYDROXY-3,5,6,8,10,12,14-HEPTAMETHYL-1-OXA-6-AZACYCLOPENTADECAN-15-ONE;CS-O-07325;DESOSAMINYLAZITHROMYCIN [USP-RS];AZITHROMYCIN IMPURITY J [EP IMPURITY];A898968;Q27276847;1-OXA-6-AZACYCLOPENTADECAN-15-ONE, 2-ETHYL-3,4,10,13-TETRAHYDROXY-3,5,6,8,10,12,14-HEPTAMETHYL-11-((3,4,6-TRIDEOXY-3-(DIMETHYLAMINO)-.BETA.-D-XYLO-HEXOPYRANOSYL)OXY)-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-;1-OXA-6-AZACYCLOPENTADECAN-15-ONE, 2-ETHYL-3,4,10,13-TETRAHYDROXY-3,5,6,8,10,12,14-HEPTAMETHYL-11-((3,4,6-TRIDEOXY-3-(DIMETHYLAMINO)-.BETA.-D-XYLO-HEXOPYRANOSYL)OXY)-, (2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*))-

Chemical Property of Desosaminylazithromycin

Chemical Property:

• Boiling Point: 727.3±60.0 °C(Predicted)
• PKA: 13.29±0.70(Predicted)
• PSA: 152.39000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 0.91340
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 590.41423143
• Heavy Atom Count: 41
• Complexity: 849

Purity/Quality:

97% ^*data from raw suppliers

DescladinoseAzithromycin ^*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)O)C)OC2C(C(CC(O2)C)N(C)C)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)O[C@H]2[C@@H]([C@H](C[C@H](O2)C)N(C)C)O)(C)O)C)C)C)O)(C)O
• Uses: Descladinose Azithromycin is a metabolite of the semi-synthetic macrolide antibiotic Azithromycin (A927000). Descladinose Azithromycin (Azithromycin EP Impurity J) is a metabolite of the semi-synthetic macrolide antibiotic Azithromycin (A927000).

Technology Process of Desosaminylazithromycin

There total 5 articles about Desosaminylazithromycin 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: 92.1%

Zithromax(R) (83905-01-5,92470-27-4) → (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)‐11-((2S,3R,4S,6R)‐4-dimethylamino-3-hydroxy-6-methyl-tetrahydropyran-2-yloxy)-2-ethyl-3,4,10,13-tetrahydroxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopetadecan-15-one (117693-41-1)

Guidance literature:

Zithromax(R); With hydrogenchloride; In methanol; water; at 20 ℃; for 24h; pH=1 - 1.5;

With sodium hydroxide; In ethanol; water; at 20 ℃; for 24h; pH=10.5 - 11;

DOI:10.1016/j.ejmech.2009.11.032

Reference yield: 67.0%

azithromycin → (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)‐11-((2S,3R,4S,6R)‐4-dimethylamino-3-hydroxy-6-methyl-tetrahydropyran-2-yloxy)-2-ethyl-3,4,10,13-tetrahydroxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopetadecan-15-one (117693-41-1)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 24h; pH=1;

DOI:10.1016/j.bmcl.2021.128330

Reference yield: 58.0%

Zithromax(R) (83905-01-5,92470-27-4) → cladinose (3758-45-0,470-12-2) + (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)‐11-((2S,3R,4S,6R)‐4-dimethylamino-3-hydroxy-6-methyl-tetrahydropyran-2-yloxy)-2-ethyl-3,4,10,13-tetrahydroxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopetadecan-15-one (117693-41-1)

Guidance literature:

With hydrogenchloride; In water; acetone;

DOI:10.1039/c4md00220b

upstream raw materials:

Zithromax(R)

Downstream raw materials:

C₄₃H₇₁N₃O₁₁