204255-02-7

Basic information

• Product Name: ETHYL (1R,5R,6R)-5-(1-ETHYLPROPOXY)-7-AZABICYCLO[4.1.0]HEPT-3-ENE-3-CARBOXYLATE
• Synonyms: ETHYL (1R,5R,6R)-5-(1-ETHYLPROPOXY)-7-AZABICYCLO[4.1.0]HEPT-3-ENE-3-CARBOXYLATE;(1R,5R,6R)-5-(1-ethylpropoxy)-7-Azabicyclo[4.1.0]hept-3-ene-3-carboxylicacid, ethyl ester;ethyl (3R,4R,5R)-4,5-iMino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
• CAS NO: 204255-02-7
• Molecular Formula: C₁₄H₂₃NO₃
• Molecular Weight: 253.34
• Product Categories: Amines;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 204255-02-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 110.0 °C
• Boiling Point: 335.5±42.0 °C(Predicted)
• Appearance: /
• Density: 1.07±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 5.80±0.60(Predicted)
• CAS DataBase Reference: ETHYL (1R,5R,6R)-5-(1-ETHYLPROPOXY)-7-AZABICYCLO[4.1.0]HEPT-3-ENE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL (1R,5R,6R)-5-(1-ETHYLPROPOXY)-7-AZABICYCLO[4.1.0]HEPT-3-ENE-3-CARBOXYLATE(204255-02-7)
• EPA Substance Registry System: ETHYL (1R,5R,6R)-5-(1-ETHYLPROPOXY)-7-AZABICYCLO[4.1.0]HEPT-3-ENE-3-CARBOXYLATE(204255-02-7)

Safety Data

• Hazardous Substances Data: 204255-02-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Intermediate in the production of Oseltamivir.

Upstream product

• 204254-98-8 ethyl-(3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 
• 77-76-9 2,2-dimethoxy-propane 
• 77-95-2 D-(-)-quinic acid 
• 204254-81-9 ethyl (3aR,5S,7R,7aR)-5-hydroxy-7-methanesulfonyloxy-2,2-dimethylhexahydrobenzo[1,3]dioxole-5-carboxylate 
• 204254-90-0 ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate 
• 204254-84-2 ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate 
• 204254-96-6 (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester 

Downstream Products

• 204255-04-9 ethyl-(3R,4R,5S)-4-amino-5-azido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 
• 1362750-72-8 C₁₈H₂₈N₄O₄ 
• 1362750-75-1 C₂₁H₃₇N₂O₄P 
• 1362750-99-9 C₂₁H₃₆N₂O₄ 
• 196618-13-0 oseltamivir 
• 204255-09-4 oseltamivir hydrochloride 
• 1163128-59-3 ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate 
• 1364932-19-3 (3R,4R,5S)-5-(acetylamino)-4-amino-3-(pentan-3-yloxy) cyclohex-1-ene-1-carboxylic acid 
• 204255-11-8 oseltamivir phosphate 
• 204255-06-1 oseltamivir 

Relevant articles and documents

Synthesis and characterization of potential pharmacopeial impurities of oseltamivir: An antiviral drug

Impurities of oseltamivir phosphate were synthesized from chiral epoxide (1) in a simpler and much feasible synthetic approach in seven steps accounting to 8.2 % overall yield. The nucleophilic addition of N3 (highly regioselective and stereoselective) in

Synthesis and in vitro study of novel neuraminidase inhibitors against avian influenza virus

Evidences of oseltamivir resistant influenza patients raised the need of novel neuraminidase inhibitors. In this study, five oseltamivir analogs PMC-31-PMC-36, synthesised according to the outcomes of a rational design analysis aimed to investigate the effects of substitution at the 5-amino and 4-amido groups of oseltamivir on its antiviral activity, were screened for their inhibition against neuraminidase N1 and N3. The enzymes used as models were from the avian influenza A H7N1 and H7N3 viruses. The neuraminidase inhibition assay was carried out by using recombinant species obtained from a baculovirus expression system and the fluorogenic substrate MUNANA. The assay was validated by using oseltamivir carboxylate as a reference inhibitor. Among the tested compounds, PMC-36 showed the highest inhibition on N1 with an IC50 of 14.6 ± 3.0 nM (oseltamivir 25 ± 4 nM), while PMC-35 showed a significant inhibitory effect on N3 with an IC50 of 0.1 ± 0.03 nM (oseltamivir 0.2 ± 0.02 nM). The analysis of the inhibitory properties of this panel of compounds allowed a preliminary assessment of a structure-activity relationship for the modification of the 4-amido and 5-amino groups of oseltamivir carboxylate. The substitution of the acetamido group in the oseltamivir structure with a 2-butenylamido moiety reduced the observed activity, while the introduction of a propenylamido group was well tolerated. Substitution of the free 5-amino group of oseltamivir carboxylate with an azide, decreased the activity against both N1 and N3. When these structural changes were both introduced, a dramatic reduction of activity was observed for both N1 and N3. The alkylation of the free 5-amino group in oseltamivir carboxylate introducing an isopropyl group seemed to increase the inhibitory effect for both N1 and N3 neuraminidases, displaying a more pronounced effect against N1.

Practical Total Synthesis of the Anti-Influenza Drug GS-4104

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