ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate

Base Information

• Chemical Name: ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate
• CAS No.: 1163128-59-3
• Molecular Formula: C₁₉H₃₂N₄O₅
• Molecular Weight: 396.487
• Mol file: 1163128-59-3.mol

Synonyms:ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate

Chemical Property of ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate

There total 19 articles about ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)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: 89.0%

7-tert-butyl 3-ethyl (1R,5R,6R)-5-(1-ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3,7-dicarboxylate → ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate (1163128-59-3)

Guidance literature:

With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; at 90 ℃; for 6h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2015.02.081

Reference yield: 80.0%

2-pentanol (584-02-1) + C14H20N4O4 (1163128-58-2) → ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate (1163128-59-3)

Guidance literature:

With boron trifluoride diethyl etherate; at -20 ℃; for 2h;

Reference yield: 68.0%

ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate (1401454-88-3) → ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate (1163128-59-3)

Guidance literature:

With sodium azide; In water; N,N-dimethyl-formamide; at 90 ℃; for 8h;

DOI:10.1016/j.tet.2015.02.081

upstream raw materials:

2-pentanol

C₁₄H₂₀N₄O₄

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

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

Downstream raw materials:

oseltamivir

oseltamivir phosphate

oseltamivir

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