1402431-91-7

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate is used as an antiviral agent for the treatment of influenza. As a stereoisomer of Oseltamivir, it plays a crucial role in inhibiting the neuraminidase enzyme of the influenza virus, thereby preventing the spread of the virus within the host.
Used in Antiviral Research:
ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate is also used in the research and development of new antiviral drugs. Its structural similarity to Oseltamivir makes it a valuable candidate for studying the structure-activity relationship of neuraminidase inhibitors, potentially leading to the discovery of more effective antiviral medications.
Used in Drug Synthesis:
Ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate can be utilized as a key intermediate in the synthesis of other antiviral drugs. Its unique stereochemistry and functional groups make it a versatile building block for the development of novel pharmaceutical compounds targeting viral infections.

Upstream product

• 1401454-83-8 (2R,3S)-1-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-((R)-3-(ethoxycarbonyl)-1-(methanesulfonyloxy)but-3-en-1-yl)-aziridine-1-carboxylate 
• 1401454-84-9 C₁₆H₂₇NO₈S 
• 1401454-85-0 (2S,3R)-tert-butyl 2-((R)-3-(ethoxycarbonyl)-1-(methanesulfonyloxy)but-3-en-1-yl)-3-formylaziridine-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 
• 1132659-99-4 (3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 1132659-98-3 (3R,4S,5R)-4-amino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 1401454-81-6 (2R,3S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-((R)-3-(ethoxycarbonyl)-1-hydroxybut-3-en-1-yl)aziridine-1-carboxylate 
• 1226768-14-4 N-((2R,3S)-1-nitro-4-oxo-3-(pentan-3-yloxy)butan-2-yl)acetamide 
• 1141364-90-0 2-(pentan-3-yloxy)acetaldehyde 
• 584-02-1 2-pentanol 
• 949164-64-1 ethyl (3R,4R,5S)-4-acetamido-5-nitro-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 
• 1226768-17-7 ethyl (3R,4R,5R)-4-acetamido-5-nitro-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 

Downstream Products

• 204255-11-8 oseltamivir phosphate 
• 187227-45-8 (3R,4R,5R)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid 

Relevant academic research and scientific papers

Preparation method of oseltamivir chiral impurities

The invention relates to a preparation method of an oseltamivir chiral impurity as shown in a formula 7. The method includes the steps: (a) attacking epoxy from back surface by a compound 1 through sodium azide under the action of ammonium chloride, and s

Stereoisomers of oseltamivir-synthesis, in silico prediction and biological evaluation

Oseltamivir is an important antiviral drug, which possess three chirality centers in its structure. From eight possible stereoisomers, only two have been synthesized and evaluated so far. We describe herein the stereoselective synthesis, computational activity prediction and biological testing of another three diastereoisomers of oseltamivir. These isomers have been synthesized using stereoselective organocatalytic Michael addition, cyclization and reduction. Their binding to viral neuraminidase N1 of influenza A virus was evaluated by quantum-chemical calculations and their anti-influenza activities were tested by an in vitro virus-inhibition assay. All three isomers displayed antiviral activity lower than that of oseltamivir, however, one of the stereoisomers, (3S,4R,5S)-isomer, of oseltamivir showed in vitro potency towards the Tamiflu-sensitive influenza viral strain A/Perth/265/2009(H5N1) comparable to Tamiflu.

Multistep Continuous-Flow Synthesis of (-)-Oseltamivir

A continuous-flow synthesis of (-)-oseltamivir composed of five flow units was accomplished. In each unit, the following reactions proceed efficiently: (1) a diphenylprolinol silyl ether mediated Michael reaction, (2) a domino reaction of Michael and intermolecular Horner-Wadsworth-Emmons reactions, (3) protonation, (4) epimerization, and (5) reduction of a nitro group to an amine. (-)-Oseltamivir was obtained in 13% total yield through a single flow with a residence time of 310 minutes.

Time Economical Total Synthesis of (-)-Oseltamivir

A time economical 60 min total synthesis of (-)-oseltamivir was accomplished in a single reaction vessel over five steps. One of the key issues is reduction in the number of steps by eliminating lengthy reaction steps with substitution of a rapid epimerization step. A catalytic system consisting of three reagents, namely, diphenylprolinol silyl ether, thiourea, and acid, was developed for a rapid asymmetric Michael reaction with excellent diastereo- and enantioselectivities. All reactions were optimized in terms of not only yield and selectivity but also reaction time.

Synthesis of (-)-oseltamivir phosphate (tamiflu) starting from cis-2,3-bis(hydroxymethyl)aziridine

Oseltamivir phosphate (Tamiflu) has been synthesized from cis-2,3-bis(hydroxymethyl)aziridine. After protection of the cis-2,3-bis(hydroxymethyl)aziridine with a Boc group, desymmetrization provided a chiral aziridine, which was a key intermediate to install the required stereogenic center containing a nitrogen atom. Allylation and ring closing metathesis are the key reactions to obtain the cyclic product that was successfully converted to the desired oseltamivir phosphate.