ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Base Information

• Chemical Name: ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• CAS No.: 1402431-91-7
• Molecular Formula: C₁₆H₂₈N₂O₄
• Molecular Weight: 312.409
• Mol file: 1402431-91-7.mol

Synonyms:ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Chemical Property of ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Chemical Property:

• Boiling Point: 473.3±45.0 °C(Predicted)
• Density: 1.08±0.1 g/cm3(Predicted)

Purity/Quality:

NLT 98% ^*data from raw suppliers

(3R,4R,5R)-Ethyl4-Acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (3R,4R,5R)-Ethyl 4-Acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate is a stereoisomer of Oseltamivir (O701005), an important antiviral drug and an orally active inhibitor of influenza virus neuraminidase.

Technology Process of ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

There total 24 articles about ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.4%

C21H36N2O6 → ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (1402431-91-7)

Guidance literature:

With hydrogenchloride; In ethanol; at 20 ℃; for 16h;

Reference yield:

(3R,4R)-ethyl 4-acetamido-5-nitro-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate → ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (1402431-91-7) + oseltamivir (196618-13-0)

Guidance literature:

With chloro-trimethyl-silane; ethanol; zinc; In tetrahydrofuran; toluene; at 70 ℃; for 2h; Flow reactor;

DOI:10.1055/s-2016-0036-1588899

Reference yield:

ethyl (3R,4R,5R)-4-acetamido-5-nitro-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (1226768-17-7) → ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (1402431-91-7)

Guidance literature:

With hydrogenchloride; In water; at 50 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01595

upstream raw materials:

(2R,3S)-1-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-((R)-3-(ethoxycarbonyl)-1-(methanesulfonyloxy)but-3-en-1-yl)-aziridine-1-carboxylate

C₁₆H₂₇NO₈S

(2S,3R)-tert-butyl 2-((R)-3-(ethoxycarbonyl)-1-(methanesulfonyloxy)but-3-en-1-yl)-3-formylaziridine-1-carboxylate

tert-butyl (2S,3S)-2-ethenyl-3-{(1R)-3-(ethoxycarbonyl)-1-[(methylsulfonyl)oxy]but-3-en-1-yl}aziridine-1-carboxylate

Downstream raw materials:

oseltamivir phosphate

(3R,4R,5R)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid

Refernces

• 1、 Hajzer, Viktória,Fi?era, Roman,Latika, Attila,Durmis, Július,Kollár, Jakub,Frecer, Vladimír,Tu?eková, Zuzana,Miertu?, Stanislav,Kostolansky, Franti?ek,Vare?ková, Eva,?ebesta, Radovan. "Stereoisomers of oseltamivir-synthesis, in silico prediction and biological evaluation". . p. 1828 - 1841. Retrieved 2017/03/09.
• 2、 Hayashi, Yujiro,Ogasawara, Shin. "Time Economical Total Synthesis of (-)-Oseltamivir". . p. 3426 - 3429. Retrieved 2016/07/26.