204254-98-8

Basic information

• Product Name: ETHYL (3R,4S,5R)-5-AZIDO-3-(1-ETHYLPROPOXY)-4-HYDROXYCYCLOHEX-1-ENE-1-CARBOXYLATE
• Synonyms: ETHYL (3R,4S,5R)-5-AZIDO-3-(1-ETHYLPROPOXY)-4-HYDROXYCYCLOHEX-1-ENE-1-CARBOXYLATE
• CAS NO: 204254-98-8
• Molecular Formula: C14H23N3O4
• Molecular Weight: 0
• Mol File: 204254-98-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ETHYL (3R,4S,5R)-5-AZIDO-3-(1-ETHYLPROPOXY)-4-HYDROXYCYCLOHEX-1-ENE-1-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL (3R,4S,5R)-5-AZIDO-3-(1-ETHYLPROPOXY)-4-HYDROXYCYCLOHEX-1-ENE-1-CARBOXYLATE(204254-98-8)
• EPA Substance Registry System: ETHYL (3R,4S,5R)-5-AZIDO-3-(1-ETHYLPROPOXY)-4-HYDROXYCYCLOHEX-1-ENE-1-CARBOXYLATE(204254-98-8)

Safety Data

• Hazardous Substances Data: 204254-98-8(Hazardous Substances Data)

Usage

Uses

(3R,4S,5R)-Ethyl 5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate is an intermediate in the synthesis of (1R,5R,6R)-5-(1-Ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylic Acid Ethyl Ester (E925510), an intermediate in the production of Oseltamivir.

Upstream product

• 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 
• 204254-90-0 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 
• 204254-81-9 ethyl (3aR,5S,7R,7aR)-5-hydroxy-7-methanesulfonyloxy-2,2-dimethylhexahydrobenzo[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

• 204255-02-7 ethyl-(1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate 
• 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 

Relevant articles and documents

Preparation method of oseltamivir enantiomer

The invention relates to a preparation method of an oseltamivir enantiomer as shown in a formula I. The method includes the steps: attacking epoxy from back surface by a compound II through sodium azide under the action of ammonium chloride to obtain a compound III; catalyzing the compound III to obtain a compound IV; treating the compound IV under the actions of triethyl silicane and titanium tetrachloride to obtain a compound V; reducing azide by the compound V under the action of triphenylphosphine, and performing loop closing on the compound V and adjacent hydroxyls to obtain a compound VI; attacking cyclamine to open rings from back surface by the compound VI through sodium azide under the action of ammonium chloride, simultaneously overturning a configuration, and performing acetylation by the aid of acetic anhydride to obtain a compound VII; performing Staudinger reaction on the compound VII under the action of triphenylphosphine to reduce the azide into amino to obtain the oseltamivir enantiomer as shown in the formula I. The preparation method of the oseltamivir enantiomer has significance for quality research and quality control of oseltamivir phosphate.

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.