[(1S,5R,6R)-6-acetamido-3-ethoxycarbonyl-5-pentan-3-yloxycyclohex-3-en-1-yl]azanium;dihydrogen phosphate

Base Information

• Chemical Name: [(1S,5R,6R)-6-acetamido-3-ethoxycarbonyl-5-pentan-3-yloxycyclohex-3-en-1-yl]azanium;dihydrogen phosphate
• CAS No.: 204255-11-8
• Molecular Formula: C16H28N2O4^.H3PO4
• Molecular Weight: 410.404
• Hs Code.: 2924299500
• Mol file: 204255-11-8.mol

Synonyms:[(1S,5R,6R)-6-acetamido-3-ethoxycarbonyl-5-pentan-3-yloxycyclohex-3-en-1-yl]azanium;dihydrogen phosphate

Chemical Property of [(1S,5R,6R)-6-acetamido-3-ethoxycarbonyl-5-pentan-3-yloxycyclohex-3-en-1-yl]azanium;dihydrogen phosphate

Chemical Property:

• Appearance/Colour: white cyrstalline solid
• Melting Point: 196-198°C
• Boiling Point: 473.3 °C at 760 mmHg
• Flash Point: 240 °C
• PSA: 178.22000
• Density: 1.08g/cm3
• LogP: 1.44800
• Storage Temp.: -20°C Freezer
• Solubility.: H2O: soluble30mg/mL, clear
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 410.18180295
• Heavy Atom Count: 27
• Complexity: 468

Purity/Quality:

99%, ^*data from raw suppliers

Oseltamivir phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC)OC1C=C(CC(C1NC(=O)C)[NH3+])C(=O)OCC.OP(=O)(O)[O-]
• Isomeric SMILES: CCC(CC)O[C@@H]1C=C(C[C@@H]([C@H]1NC(=O)C)[NH3+])C(=O)OCC.OP(=O)(O)[O-]
• General Description: Oseltamivir phosphate is a neuraminidase inhibitor widely used as an antiviral drug for the treatment and prophylaxis of influenza A and B infections, including highly pathogenic strains such as H5N1. It serves as a prodrug, metabolized in vivo to its active form, oseltamivir carboxylate, which competitively inhibits viral neuraminidase, preventing viral release from infected cells. Recent research has explored N-substituted derivatives of oseltamivir to enhance potency and selectivity against H5N1 neuraminidase, with some compounds demonstrating superior activity compared to oseltamivir carboxylate, including improved efficacy against resistant strains like the H274Y mutant. These advancements highlight its continued relevance as a scaffold for developing next-generation influenza therapeutics.

Technology Process of [(1S,5R,6R)-6-acetamido-3-ethoxycarbonyl-5-pentan-3-yloxycyclohex-3-en-1-yl]azanium;dihydrogen phosphate

There total 179 articles about [(1S,5R,6R)-6-acetamido-3-ethoxycarbonyl-5-pentan-3-yloxycyclohex-3-en-1-yl]azanium;dihydrogen phosphate 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%

oseltamivir (196618-13-0) → oseltamivir phosphate (204255-11-8)

Guidance literature:

With phosphoric acid; In ethanol; at 50 ℃; for 0.0166667h; Sonication;

Reference yield: 92.0%

oseltamivir (204255-06-1) → oseltamivir phosphate (204255-11-8)

Guidance literature:

oseltamivir; With tributylphosphine; triphenylphosphine; In ethanol; water; at 50 ℃; for 3h;

With phosphoric acid; In ethanol;

Reference yield: 88.0%

phosphoric acid (86119-84-8,7664-38-2) + oseltamivir (196618-13-0) → oseltamivir phosphate (204255-11-8)

Guidance literature:

In ethanol; water; at 50 - 55 ℃; for 1.5 - 2h;

upstream raw materials:

oseltamivir

tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate

ethanol

(1S,2R)-2-(acetylamino)-1-(tert-butoxycarbonylamino)-4-cyclohexen-3-one

Downstream raw materials:

(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

(3R,4R,5S)-4-acetamido-N-(1'-deoxylactitol-1'-yl)-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylic acid

(3R,4R,5S)-ethyl 4-acetamido-N-(1'-deoxylactitol-1'-yl)-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

(3R,4R,5S)-ethyl 4-acetamido-5-lactobionamido-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Refernces

Discovery of N-substituted oseltamivir derivatives as potent and selective inhibitors of H5N1 influenza neuraminidase

10.1021/jm500892k

The research focused on the discovery of N-substituted oseltamivir derivatives as potent and selective inhibitors of H5N1 influenza neuraminidase. The study was motivated by the increasing concern of another global flu pandemic, particularly the threat posed by the highly pathogenic avian influenza A (H5N1) virus. The researchers designed and synthesized two series of oseltamivir derivatives targeting the 150-cavity of Group-1 neuraminidase (NA) enzymes, which are especially involved in combating the H5N1 virus. The most potent N1-selective inhibitor among these compounds was compound 20l, with IC50 values of 0.0019 μM, 0.0038 μM, and 0.0067 μM against NAs from three H5N1 viruses, outperforming oseltamivir carboxylate. Another notable compound was compound 32, which exhibited a 12-fold increase in activity against the H274Y mutant relative to oseltamivir carboxylate. The study utilized various chemicals in the synthesis process, including oseltamivir phosphate as the primary starting material, aldehydes for the formation of key intermediates, and reagents such as NaBH3CN, (Boc)2O, and TFA for different synthetic steps. The research also involved the use of 2′-(4-methylumbelliferyl)-α-D-N-acetylneuraminic acid (MUNANA) as a substrate in the neuraminidase inhibition assay to evaluate the inhibitory activities of the synthesized compounds. The findings represent a significant breakthrough in the development of potent Group-1-specific neuraminidase inhibitors, which could be further investigated for the treatment of H5N1 virus infections.