diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate

Base Information

Chemical Name:diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate
CAS No.:1062100-87-1
Molecular Formula:C₂₂H₄₁N₂O₇P
Molecular Weight:476.55
Hs Code.:

Synonyms:diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate

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Chemical Property of diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate

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Technology Process of diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate

There total 7 articles about diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate 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: 85.0%

: 1062100-84-8
(3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-bromocyclohexene

: 762-04-9
phosphonic acid diethyl ester

: 1062100-87-1
diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate

Guidance literature:: With 1,4-diaza-bicyclo[2.2.2]octane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 90 ℃; for 12h;
DOI:10.1002/anie.200801959

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: C₁₇H₃₃N₂O₅P

: 1062100-87-1
diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate

: diethyl (3R,4R,5R)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate

Guidance literature:: With triethylamine; In dichloromethane; at 25 ℃; for 18h;
DOI:10.1016/j.tet.2014.11.062

Reference yield:

: 196618-13-0
oseltamivir

: 1062100-87-1
diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydrogencarbonate / tetrahydrofuran; water / 2 h / 25 °C

2.1: potassium hydroxide / methanol; water / 2 h / 25 °C

3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; dmap / dichloromethane / 0.5 h / 25 °C

3.2: 3 h / 25 °C

4.1: 1,1,2-trifluoro-1-iodoethane / dichloromethane / 0.5 h / 25 °C / Photolysis

5.1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 3 h / 90 °C / Inert atmosphere

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,1,2-trifluoro-1-iodoethane; sodium hydrogencarbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1016/j.ejmech.2014.04.082