(2S,3S)-2-{(S)-2-[(R)-1-(2,2-Dimethyl-propionylamino)-ethyl]-benzenesulfinyl}-3-hydroxy-3-(4-nitro-phenyl)-propionic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3S)-2-{(S)-2-[(R)-1-(2,2-Dimethyl-propionylamino)-ethyl]-benzenesulfinyl}-3-hydroxy-3-(4-nitro-phenyl)-propionic acid tert-butyl ester
• CAS No.: 144434-06-0
• Molecular Formula: C₂₆H₃₄N₂O₇S
• Molecular Weight: 518.631
• Mol file: 144434-06-0.mol

Synonyms:(2S,3S)-2-{(S)-2-[(R)-1-(2,2-Dimethyl-propionylamino)-ethyl]-benzenesulfinyl}-3-hydroxy-3-(4-nitro-phenyl)-propionic acid tert-butyl ester

Chemical Property of (2S,3S)-2-{(S)-2-[(R)-1-(2,2-Dimethyl-propionylamino)-ethyl]-benzenesulfinyl}-3-hydroxy-3-(4-nitro-phenyl)-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-{(S)-2-[(R)-1-(2,2-Dimethyl-propionylamino)-ethyl]-benzenesulfinyl}-3-hydroxy-3-(4-nitro-phenyl)-propionic acid tert-butyl ester

There total 7 articles about (2S,3S)-2-{(S)-2-[(R)-1-(2,2-Dimethyl-propionylamino)-ethyl]-benzenesulfinyl}-3-hydroxy-3-(4-nitro-phenyl)-propionic acid tert-butyl 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: 70.0%

4-nitrobenzaldehdye (555-16-8) + (S(S)R)-tert-butyl o-<1-(tert-butylcarbonylamino)ethyl>phenylsulfinylacetate (139223-54-4) → (2S,3S)-2-{(S)-2-[(R)-1-(2,2-Dimethyl-propionylamino)-ethyl]-benzenesulfinyl}-3-hydroxy-3-(4-nitro-phenyl)-propionic acid tert-butyl ester (144434-06-0)

Guidance literature:

With tert-butylmagnesium bromide; In tetrahydrofuran; 1) 6 h, -78 deg C, 2) 6 h, r.t.;

DOI:10.1016/S0040-4039(00)79112-X

Reference yield:

(R)-(+)-o-(1-pivaloylaminoethyl)thiophenol (144434-12-8) → (2S,3S)-2-{(S)-2-[(R)-1-(2,2-Dimethyl-propionylamino)-ethyl]-benzenesulfinyl}-3-hydroxy-3-(4-nitro-phenyl)-propionic acid tert-butyl ester (144434-06-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) sodium periodate, 2.) sodium hydroxide / 1.) iodine / 1.) MeOH, H₂O, reflux, 16 h, 2.) THF, H₂O, 1.0 h

2: 67 percent / SOCl₂, DMAP / tetrahydrofuran / 18 h / Ambient temperature

3: 1.) EtMgBr, diisopropylamine / 1.) Et₂O, reflux, 1 h, 2.) THF, Et₂O, -40 deg C, 4 h

4: 1.) tert-BuMgBr / 1.) Et₂O, THF, -78 deg C, 1.5 h, 2.) THF, a) -78 deg C, 4 h, b) -78 deg C -> ambient temperature, ca. 16 h

With dmap; sodium hydroxide; sodium periodate; thionyl chloride; tert-butylmagnesium bromide; ethylmagnesium bromide; diisopropylamine; iodine; In tetrahydrofuran;

Reference yield:

(R)-1-phenyl-ethyl-amine (3886-69-9) → (2S,3S)-2-{(S)-2-[(R)-1-(2,2-Dimethyl-propionylamino)-ethyl]-benzenesulfinyl}-3-hydroxy-3-(4-nitro-phenyl)-propionic acid tert-butyl ester (144434-06-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

2: 1.) tert-BuLi, 2.) SO₂ / 1.) Et₂O, a) -78 deg C, 1 h, b) 0 deg C, 0.5 h, 2.) -78 deg C -> ambient temperature

3: 67 percent / SOCl₂, DMAP / tetrahydrofuran / 18 h / Ambient temperature

4: 1.) EtMgBr, diisopropylamine / 1.) Et₂O, reflux, 1 h, 2.) THF, Et₂O, -40 deg C, 4 h

5: 1.) tert-BuMgBr / 1.) Et₂O, THF, -78 deg C, 1.5 h, 2.) THF, a) -78 deg C, 4 h, b) -78 deg C -> ambient temperature, ca. 16 h

With dmap; thionyl chloride; tert-butylmagnesium bromide; sulfur dioxide; ethylmagnesium bromide; tert.-butyl lithium; triethylamine; diisopropylamine; In tetrahydrofuran; dichloromethane;

upstream raw materials:

4-nitrobenzaldehdye

(S_(S)R)-tert-butyl o-<1-(tert-butylcarbonylamino)ethyl>phenylsulfinylacetate

(R)-1-phenyl-ethyl-amine

(R)-(+)-N-(1-phenylethyl)-2,2-dimethylpropanamide