204255-06-1

Basic information

• Product Name: ETHYL (3R,4R,5S)-4-ACETAMIDO-5-AZIDO-3-(1-ETHYLPROPOXY)CYCLOHEX-1-ENE-1-CARBOXYLATE
• Synonyms: ETHYL (3R,4R,5S)-4-ACETAMIDO-5-AZIDO-3-(1-ETHYLPROPOXY)CYCLOHEX-1-ENE-1-CARBOXYLATE;5-Azido Oseltamivir;Ethyl (3R,4R,5S)-4-acetamido-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate;(3R,4R,5S)-4-(AcetylaMino)-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic Acid Ethyl Ester;[3R-(3α,4β,5α)]-4-(AcetylaMino)-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic Acid Ethyl Ester;Ethyl(3R,4R,5S)-4-N-AcetaMido-5-azido-3- (1-ethylpropoxy)-1-cyclohexene-1-carboxylate;(3R,4R,5S)-4-Acetylamino-5-azido-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl este
• CAS NO: 204255-06-1
• Molecular Formula: C₁₆H₂₆N₄O₄
• Molecular Weight: 0
• EINECS: 1592732-453-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 204255-06-1.mol
• Article Data: 32

Chemical Properties

• Melting Point: 135-137°C
• Appearance: /
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform, DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: ETHYL (3R,4R,5S)-4-ACETAMIDO-5-AZIDO-3-(1-ETHYLPROPOXY)CYCLOHEX-1-ENE-1-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL (3R,4R,5S)-4-ACETAMIDO-5-AZIDO-3-(1-ETHYLPROPOXY)CYCLOHEX-1-ENE-1-CARBOXYLATE(204255-06-1)
• EPA Substance Registry System: ETHYL (3R,4R,5S)-4-ACETAMIDO-5-AZIDO-3-(1-ETHYLPROPOXY)CYCLOHEX-1-ENE-1-CARBOXYLATE(204255-06-1)

Safety Data

• Hazardous Substances Data: 204255-06-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

InChI:InChI=1/C16H26N4O4/c1-5-12(6-2)24-14-9-11(16(22)23-7-3)8-13(19-20-17)15(14)18-10(4)21/h9,12-15H,5-8H2,1-4H3,(H,18,21)/t13-,14+,15+/m0/s1

Upstream product

• 584-02-1 2-pentanol 
• 1350928-94-7 C₉H₁₂O₆S 
• 1268086-96-9 ethyl (3R,4R,5R)-4,5-acetylimino-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate 
• 1388051-82-8 ethyl (3R,4S,5R)-3,4-O-thionyl-5-O-methanesulfonylshikimate 
• 1388051-86-2 ethyl (3S,4R,5R)-3-azido-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate 
• 1401454-86-1 tert-butyl (2S,3S)-2-ethenyl-3-{(1R)-3-(ethoxycarbonyl)-1-[(methylsulfonyl)oxy]but-3-en-1-yl}aziridine-1-carboxylate 
• 1401454-87-2 ethyl (1S,5R,6S)-7-(tert-butoxycarbonyl)-5-(methanesulfonyloxy)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate 
• 1401454-88-3 ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate 
• 1163128-59-3 ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate 
• 1151665-76-7 ethyl (1S,5R,6S)-5-methanesulfonyloxy-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate 
• 1151665-77-8 (1S,5R,6S)-ethyl 7-acetyl-5-((methylsulfonyl)oxy)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate 

Downstream Products

• 1363339-68-7 PMC-34 
• 1362750-80-8 C₁₉H₃₅N₂O₄P 
• 204255-11-8 oseltamivir phosphate 
• 204255-09-4 oseltamivir hydrochloride 
• 1588477-09-1 ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-methylguanidino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 1588477-08-0 (3R,4R,5S)-ethyl 4-acetamido-5-(3-((benzyloxy)carbonyl)thioureido)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate 
• 1192537-55-5 (3R,4R,5S)-5-[[(1Z)-[[(tert-butoxy)carbonyl]amino]([[(tert-butoxy)carbonyl]imino])methyl]amino]-4-acetylamino-3-(pent-3-yloxy)cyclohexyl-1-ene-1-carboxylic acid 
• 208720-81-4 (3R,4R,5S)-5-[[(1Z)-[[(tert-butoxy)carbonyl]amino]([[(tert-butoxy)carbonyl]imino])methyl]amino]-4-acetylamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid ethyl ester 
• 1588489-28-4 (3R,4R,5S)-4-acetamido-5-((E)-2-hydroxyguanidino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylic acid trifluoroacetate 
• 1588489-27-3 (3R,4R,5S)-4-acetamido-3-(pentan-3-yloxy)-5-((E)-2-(2,2,2-trifluoroethyl)guanidino)cyclohex-1-enecarboxylic acid trifluoroacetate 
• 1588489-26-2 (3R,4R,5S)-4-acetamido-5-((E)-2-allylguanidino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylic acid trifluoroacetate 
• 1588489-25-1 (3R,4R,5S)-4-acetamido-5-((E)-2-cyclopropylguanidino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylic acid trifluoroacetate 

Relevant articles and documents

Azoacetylenes for the Synthesis of Arylazotriazole Photoswitches

We report a modular approach toward novel arylazotriazole photoswitches and their photophysical characterization. Addition of lithiated TIPS-acetylene to aryldiazonium tetrafluoroborate salts gives a wide range of azoacetylenes, constituting an underexplored class of stable intermediates.In situdesilylation transiently leads to terminal arylazoacetylenes that undergo copper-catalyzed cycloadditions (CuAAC) with a diverse collection of organoazides. These include complex molecules derived from natural products or drugs, such as colchicine, taxol, tamiflu, and arachidonic acid. The arylazotriazoles display near-quantitative photoisomerization and long thermalZ-half-lives. Using the method, we introduce for the first time the design and synthesis of a diacetylene platform. It permits implementation of consecutive and diversity-oriented approaches linking two different conjugants to independently addressable acetylenes within a common photoswitchable azotriazole. This is showcased in the synthesis of several photoswitchable conjugates, with potential applications as photoPROTACs and biotin conjugates.

FLOW SYNTHESIS PROCESS FOR THE PRODUCTION OF OSELTAMIVIR

This invention provides for a flow synthesis process for producing Oseltamivir and pharmaceutically acceptable salts thereof from shikimic acid in particular but not exclusively to a flow synthesis process for producing Oseltamivir phosphate from shikimic acid in a nine-step flow synthesis that provides for superior reaction times and product yields compared to known methods.

The hydrophobic side chain of oseltamivir influences type A subtype selectivity of neuraminidase inhibitors

Neuraminidase, which plays a critical role in the influenza virus life cycle, is a target for new therapeutic agents. The study of structure–activity relationships revealed that the C-5 position amino group of oseltamivir was pointed to 150-cavity of the neuraminidase in group 1. This cavity is important for selectivity of inhibitors against N1 versus N2 NA. A serial of influenza neuraminidase inhibitors with the oseltamivir scaffold containing lipophilic side chains at the C-5 position have been synthesized and evaluated for their influenza neuraminidase inhibitory activity and selectivity. The results indicated that compound 13o (H5N1 IC50?=?0.1?±?0.04?μm, H3N2 IC50?=?0.26?±?0.18?μm) showed better inhibitory activity and selectivity against the group 1 neuraminidase. This study may provide a clue to design of better group 1 neuraminidase inhibitors.