(3S,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile

Base Information

Chemical Name:(3S,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile
CAS No.:108868-54-8
Molecular Formula:C₁₆H₂₈N₂O₃
Molecular Weight:296.41
Hs Code.:

Synonyms:(3S,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile

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Chemical Property of (3S,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile

Chemical Property:

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Technology Process of (3S,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile

There total 8 articles about (3S,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile 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: 80.0%

: 107202-61-9
(2R,3S)-3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane

: 75-86-5
2-hydroxy-2-methylpropanenitrile

: 108868-54-8
(3S,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile

Guidance literature:: With triethylamine; In tetrahydrofuran; for 22h; Ambient temperature;
DOI:10.1016/0040-4020(96)00328-6

Reference yield: 65.0%

: 151-50-8
potassium cyanide

: 107202-61-9
(2R,3S)-3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane

: 108868-92-4
(3R,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile

: 108868-54-8
(3S,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile

Guidance literature:: In methanol; water; for 18h; Ambient temperature;
DOI:10.1021/jm00390a018

Reference yield:

: (2R,3R)-3-cyclohexyl-2,3-epoxy-1-butanol

: 108868-54-8
(3S,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / titanium diazidodiisopropoxide / benzene / 20 - 75 °C

2: 97 percent / H₂ / 10percentPd/C / ethyl acetate / 18 h / Ambient temperature

3: 76 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

4: 97 percent / triethylamine, 4-dimethylaminopyridne / CH₂Cl₂ / -15 - 20 °C

5: 1.) tetrabutylammonium fluoride, 2.) sodium methoxide / 1.) THF, RT, 30 min, 2.) THF, RT, 2 h

6: 80 percent / NEt₃ / tetrahydrofuran / 22 h / Ambient temperature

With 1H-imidazole; dmap; diisopropoxytitanium diazide; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; triethylamine; 10% palladium on active carbon; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/0040-4020(96)00328-6