(2R,4S,5S)-5-tert-Butoxycarbonylamino-2-(4-fluoro-benzyl)-4-hydroxy-6-phenyl-hexanoic acid

Base Information

Chemical Name:(2R,4S,5S)-5-tert-Butoxycarbonylamino-2-(4-fluoro-benzyl)-4-hydroxy-6-phenyl-hexanoic acid
CAS No.:150609-74-8
Molecular Formula:C₂₄H₃₀FNO₅
Molecular Weight:431.504
Hs Code.:

Synonyms:(2R,4S,5S)-5-tert-Butoxycarbonylamino-2-(4-fluoro-benzyl)-4-hydroxy-6-phenyl-hexanoic acid

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Chemical Property of (2R,4S,5S)-5-tert-Butoxycarbonylamino-2-(4-fluoro-benzyl)-4-hydroxy-6-phenyl-hexanoic acid

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Technology Process of (2R,4S,5S)-5-tert-Butoxycarbonylamino-2-(4-fluoro-benzyl)-4-hydroxy-6-phenyl-hexanoic acid

There total 10 articles about (2R,4S,5S)-5-tert-Butoxycarbonylamino-2-(4-fluoro-benzyl)-4-hydroxy-6-phenyl-hexanoic acid 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:

: 150609-73-7
(1S,2'S,4'R)-<1-<4'-(4''-fluorobenzyl)-5'-oxo-tetrahydrofuran-2'-yl>-2-phenylethyl>carbamic acid tert-butyl ester

: 150609-74-8
(2R,4S,5S)-5-tert-Butoxycarbonylamino-2-(4-fluoro-benzyl)-4-hydroxy-6-phenyl-hexanoic acid

Guidance literature:: With lithium hydroxide; In 1,2-dimethoxyethane; for 3h; Ambient temperature;
DOI:10.1021/jm00088a004

Reference yield:

: 459-31-4
3-(4-fluorophenyl)propanoic acid

: 150609-74-8
(2R,4S,5S)-5-tert-Butoxycarbonylamino-2-(4-fluoro-benzyl)-4-hydroxy-6-phenyl-hexanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: oxalyl chloride / dimethylformamide; benzene / 1.5 h / 23 °C

2: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

3: methanesulfonic acid / CH₂Cl₂ / 0.25 h / 23 °C

4: 49 percent / n-BuLi / tetrahydrofuran; hexane / a) -78 deg C, 5 min, b) 0 deg C, 1 h

5: 59 percent / p-TsOH*H₂O / CH₂Cl₂; toluene / 13 h / 23 °C

6: 1 M aq. LiOH / 1,2-dimethoxy-ethane / 0.33 h / 23 °C

With lithium hydroxide; n-butyllithium; oxalyl dichloride; methanesulfonic acid; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jm980537b

Reference yield:

: 772-70-3
3-(4-fluorophenyl)propanoyl chloride

: 150609-74-8
(2R,4S,5S)-5-tert-Butoxycarbonylamino-2-(4-fluoro-benzyl)-4-hydroxy-6-phenyl-hexanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

2: methanesulfonic acid / CH₂Cl₂ / 0.25 h / 23 °C

3: 49 percent / n-BuLi / tetrahydrofuran; hexane / a) -78 deg C, 5 min, b) 0 deg C, 1 h

4: 59 percent / p-TsOH*H₂O / CH₂Cl₂; toluene / 13 h / 23 °C

5: 1 M aq. LiOH / 1,2-dimethoxy-ethane / 0.33 h / 23 °C

With lithium hydroxide; n-butyllithium; methanesulfonic acid; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; toluene;
DOI:10.1021/jm980537b