(3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester

Base Information

• Chemical Name: (3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester
• CAS No.: 1191921-01-3
• Molecular Formula: C₁₈H₃₀N₂O₅
• Molecular Weight: 354.447
• Mol file: 1191921-01-3.mol

Synonyms:(3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester

Chemical Property of (3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Oseltamivir-acetate 99.04% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester

There total 10 articles about (3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester 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: 94.0%

acetic anhydride (108-24-7) + oseltamivir phosphate (204255-11-8) → (3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester (1191921-01-3)

Guidance literature:

oseltamivir phosphate; With dmap; triethylamine; In dichloromethane;

acetic anhydride; In dichloromethane;

DOI:10.1111/cbdd.13060

Reference yield: 74.5%

acetic acid (64-19-7,77671-22-8) + oseltamivir (196618-13-0) → (3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester (1191921-01-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; at 20 ℃;

Reference yield:

ethyl (1S,5R,6S)-5-methanesulfonyloxy-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate (1151665-76-7) → (3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester (1191921-01-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap; triethylamine

1.2: 0 - 5 °C

2.1: boron trifluoride diethyl etherate / 8 h / 0 - 20 °C / Inert atmosphere

3.1: sodium azide / water; ethanol / 8 h / 80 °C

4.1: hydrogen / ethanol / 16 h / 20 °C

4.2: 0.5 h / 50 °C

5.1: dmap; triethylamine / dichloromethane

With dmap; sodium azide; boron trifluoride diethyl etherate; hydrogen; triethylamine; In ethanol; dichloromethane; water;

DOI:10.1111/cbdd.13060

upstream raw materials:

acetic acid

oseltamivir

ethyl (1S,5R,6S)-5-methanesulfonyloxy-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate

acetic anhydride