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

Base Information

• Chemical Name: (3R,4R,5S)-ethyl 4,5-diamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• CAS No.: 212504-89-7
• Molecular Formula: C₁₄H₂₆N₂O₃
• Molecular Weight: 270.372
• Mol file: 212504-89-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (3R,4R,5S)-ethyl 4,5-diamino-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: 89.0%

(3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene (891831-20-2) + ethanol (64-17-5) → (3R,4R,5S)-ethyl 4,5-diamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (212504-89-7)

Guidance literature:

With hydrogenchloride; ammonium hydroxide;

DOI:10.1016/j.bmcl.2007.11.079

Reference yield:

ethyl (3R,4R,5S)-4,5-bis((methoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate → (3R,4R,5S)-ethyl 4,5-diamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (212504-89-7)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 40 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jacs.8b06900

Reference yield:

pentan-3-yl 2,2,2-trichloroacetimidate (949908-55-8) → (3R,4R,5S)-ethyl 4,5-diamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (212504-89-7)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluorormethanesulfonic acid / dichloromethane / 22 h / 28 °C / Molecular sieve

2: chloro-trimethyl-silane; sodium iodide / acetonitrile / 12 h / 40 °C / Inert atmosphere

With chloro-trimethyl-silane; trifluorormethanesulfonic acid; sodium iodide; In dichloromethane; acetonitrile;

DOI:10.1021/jacs.8b06900

upstream raw materials:

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

ethanol

pentan-3-yl 2,2,2-trichloroacetimidate

(±)-ethyl (1R,5R,6S)-5-acetoxy-6-nitrocyclohex-3-ene-1-carboxylate

Downstream raw materials:

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

(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

oseltamivir phosphate