(2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-(3-methoxyphenyl)butyric acid

Base Information

Chemical Name:(2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-(3-methoxyphenyl)butyric acid
CAS No.:672965-07-0
Molecular Formula:C₁₆H₂₃NO₆
Molecular Weight:325.362
Hs Code.:

Synonyms:(2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-(3-methoxyphenyl)butyric acid

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Chemical Property of (2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-(3-methoxyphenyl)butyric acid

Chemical Property:

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Technology Process of (2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-(3-methoxyphenyl)butyric acid

There total 5 articles about (2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-(3-methoxyphenyl)butyric 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: 88.0%

: 672965-06-9
Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-(3-methoxy-phenyl)-1-methylsulfanylcarbonyl-propyl ester

: 672965-07-0
(2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-(3-methoxyphenyl)butyric acid

Guidance literature:: With sodium hydroxide; In methanol; water; at 20 ℃;
DOI:10.1016/j.bmc.2003.10.037

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 672965-07-0
(2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-(3-methoxyphenyl)butyric acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylamine / tetrahydrofuran; H₂O

2.1: K₂CO₃ / dimethylformamide

3.1: sodium amide / tetrahydrofuran / 3 h / 50 °C

3.2: 59 percent / tetrahydrofuran / 2 h / 0 °C

4.1: 5.19 g / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 25 °C

5.1: 25 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / -30 - -10 °C

6.1: 88 percent / NaOH / methanol; H₂O / 20 °C

With pyridine; dmap; sodium hydroxide; potassium carbonate; sodium amide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Pummerer rearrangement;
DOI:10.1016/j.bmc.2003.10.037

Reference yield:

: (S)-2-amino-3-(3-methoxyphenyl)propanoic acid

: 672965-07-0
(2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-(3-methoxyphenyl)butyric acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylamine / tetrahydrofuran; H₂O

2.1: K₂CO₃ / dimethylformamide

3.1: sodium amide / tetrahydrofuran / 3 h / 50 °C

3.2: 59 percent / tetrahydrofuran / 2 h / 0 °C

4.1: 5.19 g / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 25 °C

5.1: 25 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / -30 - -10 °C

6.1: 88 percent / NaOH / methanol; H₂O / 20 °C

With pyridine; dmap; sodium hydroxide; potassium carbonate; sodium amide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Pummerer rearrangement;
DOI:10.1016/j.bmc.2003.10.037