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

Base Information

• Chemical Name: (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
• CAS No.: 367252-68-4
• Molecular Formula: C₂₁H₃₆N₂O₆
• Molecular Weight: 412.527

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

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

Chemical Property:

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SDS file from LookChem

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

There total 76 articles about (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + oseltamivir phosphate (204255-11-8) → (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate (367252-68-4)

Guidance literature:

oseltamivir phosphate; With sodium hydrogencarbonate; In water;

di-tert-butyl dicarbonate; With triethylamine;

DOI:10.1042/BCJ20180764

Reference yield: 96.3%

tert-butyldicarbonate (34619-03-9) + oseltamivir phosphate (204255-11-8) → (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate (367252-68-4)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 12h;

DOI:10.1016/j.ejmech.2019.111940

Reference yield: 95.0%

(3R,4R,5S)-ethyl 4-amino-5-(tert-butoxycarbonylamino)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (1012814-35-5) + acetyl chloride (75-36-5) → (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate (367252-68-4)

Guidance literature:

With pyridine; dmap; at 90 ℃; for 1h;

DOI:10.1016/j.bmcl.2008.01.037

upstream raw materials:

di-tert-butyl dicarbonate

oseltamivir

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

2-pentanol

Downstream raw materials:

oseltamivir phosphate

oseltamivir

(3R,4R,5S)-ethyl 4-acetamido-5-[(tert-butoxycarbonyl)amino]-3-(pentan-3-yloxy)-2-[2-(triethoxysilyl)ethyl]cyclohex-1-enecarboxylate

(3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid

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