367252-68-4

Basic information

• Product Name: (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
• Synonyms: (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
• CAS NO: 367252-68-4
• Molecular Weight: 412.527
• Mol File: 367252-68-4.mol
• Article Data: 42

Chemical Properties

• CAS DataBase Reference: (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate(367252-68-4)
• EPA Substance Registry System: (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate(367252-68-4)

Safety Data

• Hazardous Substances Data: 367252-68-4(Hazardous Substances Data)

Upstream product

• 891862-23-0 ethyl (1S,5S,6R)-7-acetyl-5-(tert-butoxycarbonylamino)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate 
• 584-02-1 2-pentanol 
• 1012814-35-5 (3R,4R,5S)-ethyl 4-amino-5-(tert-butoxycarbonylamino)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 204255-11-8 oseltamivir phosphate 
• 367252-67-3 (3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester 
• 507-09-5 tiolacetic acid 
• 119719-61-8 (1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one 
• 1287204-65-2 (1R,5R)-ethyl 5-hydroxycyclohex-3-enecarboxylate 
• 1287204-66-3 (1R,5S)-ethyl 5-(N-(tert-butoxycarbonyl)-4-nitrophenylsulfonamido)cyclohex-3-enecarboxylate 
• 1287204-67-4 ethyl (5S)-5-((tert-butoxycarbonyl)amino)cyclohex-3-ene-1-carboxylate 
• 1287204-68-5 (1R,3S,5S,6S)-ethyl 5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptane-3-carboxylate 

Downstream Products

• 208589-20-2 (1S,2R,3S,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-(1-ethyl-propoxy)-1,2-dihydroxy-cyclohexanecarboxylic acid ethyl ester 
• 204255-11-8 oseltamivir phosphate 
• 196618-13-0 oseltamivir 
• 764639-63-6 (3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid 
• 1122748-00-8 C₁₅H₂₉N₂O₅P 
• 1158845-41-0 C₁₉H₃₇N₂O₅P 
• 1122748-01-9 C₁₆H₃₁N₄O₅P 
• 1401808-94-3 C₁₈H₃₅N₄O₅P 
• 1062100-85-9 4-acetamido-5-(tert-butoxycarbonyl)amino-3-(1-ethylpropoxy)-1-iodo-1-cyclohexene 
• 1616373-90-0 dibutyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1616373-91-1 C₃₀H₅₇N₂O₇P 
• 1616373-92-2 di(3-phenylprop-1-yl) (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1616373-93-3 di[3-(1H-indol-3-yl)propyl] (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1616373-94-4 dibutyl (3R,4R,5S)-4-acetamido-5-[N²,N³-bis(tert-butoxycarbonyl)guanidino]-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 

Relevant articles and documents

Design, synthesis, and evaluation of carboxyl-modified oseltamivir derivatives with improved lipophilicity as neuraminidase inhibitors

In this study, a series of carboxyl-modified oseltamivir analogs with improved lipophilicity were designed and synthesized, and their inhibitory activities against neuraminidase from influenza A virus H5N1 subtype were evaluated. The results demonstrated that compound 5m exhibited potent inhibitory activity (IC50 = 1.30 ± 0.23 μM), and it targeted the recently discovered 430-cavity. Compound 5m (Log D = ?0.12) is more lipophilic than oseltamivir carboxylate (Log D = ?1.69) at pH 7.4, which is potentially propitious to improved membrane permeability and oral drug absorption. Meanwhile, 5m showed high stability in human liver microsomes. The findings of this study can be valuable in identifying neuraminidase inhibitors with optimal lipophilicity and in the exploration of 430-cavity.

Discovery of C-1 modified oseltamivir derivatives as potent influenza neuraminidase inhibitors

Inspired by our initial discovery about a series of neuraminidase (NA) inhibitors targeting the 150-cavity, in present study, we designed, synthesized, and biologically tested a panel of novel oseltamivir derivatives with C-1 modification, targeting the 430-cavity, an additional binding site which widely and stably existed in both group-1 and group-2 NAs. Some of the synthesized compounds displayed robust anti-influenza potencies against H5N1 and H5N6 viruses. Among them, compound 8b exerted the greatest inhibition, with IC50 values of 0.088 and 0.097 μM and EC50 values of 4.26 and 1.31 μM against H5N1 and H5N6 strains, respectively, which are similar to those of oseltamivir carboxylate (OSC). And its potency against mutant H5N1-H274Y NA was just 7-fold weaker than OSC. Molecular modeling revealed the elongated group at C-1 position being projected toward the 430-cavity. Notably, although compound 8b was not sensitive toward H5N1 strain relative to OSC in the embryonated egg model, it displayed greater anti-influenza virus effect against H5N6 strain than OSC at the concentration of 10 mmol/L. Overall, this work provided unique insights in the discovery of potent inhibitors against both group-1 and group-2 NAs.

A dual-functional molecular strategy for in situ suppressing and visualizing of neuraminidase in aqueous solution using iridium(III) complexes

We have designed for the first time a dual-functional luminescent probe and inhibitor of neuraminidase (NA), a key influenza target. The lead iridium(iii) complex exhibited enhanced inhibition against NA compared to the FDA-approved antiviral drug, oseltamivir, and could detect NA even in the presence of an autofluorescent background.

Expedient synthesis of oseltamivir and related compounds via direct olefin diazidation-diamidation reaction

Disclosed herein are improved methods for the preparation of oseltamivir, and intermediates useful thereto.