(3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

Base Information

Chemical Name:(3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester
CAS No.:98105-43-2
Molecular Formula:C₁₈H₃₃NO₅
Molecular Weight:343.464
Hs Code.:

Synonyms:(3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

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Chemical Property of (3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

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Technology Process of (3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

There total 23 articles about (3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester 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: 92.0%

: 112151-92-5
3-oxo-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

: 98105-43-2
(3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

Guidance literature:: With hydrogen; [(R)-BINAP]RuBr₂; In ethanol; at 18 - 21 ℃; for 145h; under 76000.1 Torr; ee = 100percent;
DOI:10.1016/S0040-4039(00)82338-2

Reference yield: 88.0%

: 127132-19-8
ethyl (3S,4S)-4-<(tert-butoxycarbonyl)amino>-3-<(tert-butyldimethylsilyl)oxy>-5-cyclohexylpentanoate

: 98105-43-2
(3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1021/jo00299a045

Reference yield:

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 98105-43-2
(3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 99.5 percent / NaHCO₃ / dimethylformamide / 120 h

2: 98.2 percent / dihydrogen / 5percent Rh/Al₂O₃ / methanol / 18 h / 1551.4 - 2844.3 Torr

3: 80 percent / diisobutylaluminum hydride (Dibal), CH₃OH / toluene; hexane / 2 h / -78 °C

4: 1.) diisopropylamine, n-BuLi / 1.) dioxane, hexane, -78 deg C, 15 min, 2.) THF, dioxane, hexane, -78 deg C, 5 min

With methanol; n-butyllithium; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; diisopropylamine; Rh/Al₂O₃; In methanol; hexane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00150a007