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

Base Information

Chemical Name:(3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene
CAS No.:927395-79-7
Molecular Formula:C₂₅H₃₅N₃O₅
Molecular Weight:457.57
Hs Code.:

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

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

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

There total 5 articles about (3R,4R,5S)-5-benzyloxycarbonylamino-4-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: 51.0%

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

: 584-02-1
2-pentanol

: 927395-76-4
(6-cyano-2-oxo-2,3,3a,4,5,7a-hexahydro-benzooxazol-4-yl)-carbamic acid benzyl ester

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

Guidance literature:: With boron trifluoride diethyl etherate; at -20 ℃; for 5h;
DOI:10.1021/ol062663c

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / LiAlH(O-t-Bu)3 / tetrahydrofuran / 2 h / -20 - 0 °C

2: 87 percent / triphenylphosphine; DEAD / tetrahydrofuran; toluene / 3 h / 0 °C

3: 51 percent / BF₃*OEt₂ / 5 h / -20 °C

With boron trifluoride diethyl etherate; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; 2: Mitsunobu reaction;
DOI:10.1021/ol062663c

Reference yield:

: 927395-57-1
(3aR,4S,7aS)-4-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-6-cyano-3a,4,5,7a-tetrahydrobenzooxazol-2-one

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

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / cesium carbonate / methanol / 3 h / 20 °C

2: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 19 h / 20 °C

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

4: 87 percent / triphenylphosphine; DEAD / tetrahydrofuran; toluene / 3 h / 0 °C

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

With boron trifluoride diethyl etherate; caesium carbonate; Dess-Martin periodane; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; 4: Mitsunobu reaction;
DOI:10.1021/ol062663c