(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene

Base Information

Chemical Name:(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene
CAS No.:927395-63-9
Molecular Formula:C₂₂H₂₉N₃O₄
Molecular Weight:399.49
Hs Code.:

Synonyms:(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene

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Technology Process of (3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene

There total 6 articles about (3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-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: 81.0%

: 927395-79-7
(3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene

: 108-24-7
acetic anhydride

: 927395-63-9
(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene

Guidance literature:: (3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 3h;

acetic anhydride; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h;
DOI:10.1021/ol062663c

Reference yield:

: 927395-61-7
(3S,4R,5S)-5-benzyloxycarbonylamino-3,4-tert-butoxycarbonylimino-1-cyanocyclohexene

: 927395-63-9
(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene

Guidance literature:: Multi-step reaction with 2 steps

1.1: 51 percent / BF₃*OEt₂ / 5 h / -20 °C

2.1: TFA / CH₂Cl₂ / 3 h / 0 - 20 °C

2.2: 81 percent / triethylamine / CH₂Cl₂ / 16 h / 0 - 20 °C

With boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/ol062663c

Reference yield:

: 927395-78-6
(4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyanocyclohexen-3-one

: 927395-63-9
(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / LiAlH(O-t-Bu)3 / tetrahydrofuran / 2 h / -20 - 0 °C

2.1: 87 percent / triphenylphosphine; DEAD / tetrahydrofuran; toluene / 3 h / 0 °C

3.1: 51 percent / BF₃*OEt₂ / 5 h / -20 °C

4.1: TFA / CH₂Cl₂ / 3 h / 0 - 20 °C

4.2: 81 percent / triethylamine / CH₂Cl₂ / 16 h / 0 - 20 °C

With boron trifluoride diethyl etherate; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; toluene; 2.1: Mitsunobu reaction;
DOI:10.1021/ol062663c