(3R,4R,5S)-4-amino-5-(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene

Base Information

• Chemical Name: (3R,4R,5S)-4-amino-5-(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene
• CAS No.: 891831-21-3
• Molecular Formula: C₁₇H₂₉N₃O₃
• Molecular Weight: 323.436
• Mol file: 891831-21-3.mol

Synonyms:(3R,4R,5S)-4-amino-5-(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene

Chemical Property of (3R,4R,5S)-4-amino-5-(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S)-4-amino-5-(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene

There total 17 articles about (3R,4R,5S)-4-amino-5-(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene 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: 63.0%

(3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene (891831-20-2) → (3R,4R,5S)-4-amino-5-(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene (891831-21-3)

Guidance literature:

(3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene; With trifluoroacetic acid; In dichloromethane; at 4 - 30 ℃; for 3h;

With di-tert-butyl dicarbonate; triethylamine; In dichloromethane; at 4 ℃; for 0.5h;

Reference yield: 63.0%

(3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene (891831-20-2) + di-tert-butyl dicarbonate (24424-99-5) → (3R,4R,5S)-4-amino-5-(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene (891831-21-3)

Guidance literature:

(3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene; With trifluoroacetic acid; In dichloromethane; at 4 - 20 ℃; for 3h;

di-tert-butyl dicarbonate; With triethylamine; In dichloromethane; at 4 ℃; for 0.5h;

DOI:10.1021/ja061696k

Reference yield:

(3S,4R,5S)-5-(tert-butoxycarbonylamino)-3,4-(tert-butoxycarbonylimino)-1-cyanocyclohexene (891831-19-9) → (3R,4R,5S)-4-amino-5-(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene (891831-21-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 52 percent / BF₃*Et₂O / 1 h / 4 °C

2.1: TFA / CH₂Cl₂ / 3 h / 4 - 20 °C

2.2: 63 percent / triethylamine / CH₂Cl₂ / 0.5 h / 4 °C

With boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja061696k

upstream raw materials:

(3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene

di-tert-butyl dicarbonate

(3S,4R,5S)-5-(tert-butoxycarbonylamino)-3,4-(tert-butoxycarbonylimino)-1-cyanocyclohexene

Downstream raw materials:

oseltamivir phosphate

oseltamivir

tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate