(2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

Base Information

• Chemical Name: (2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester
• CAS No.: 864924-29-8
• Molecular Formula: C₁₄H₁₈N₂O₆S
• Molecular Weight: 342.373
• Mol file: 864924-29-8.mol

Synonyms:(2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

Chemical Property of (2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

There total 13 articles about (2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-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: 94.0%

3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester (864924-28-7) → (2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester (864924-29-8)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 0 - 20 ℃; for 44h;

DOI:10.1021/ja051430y

Reference yield:

3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-benzaldehyde (864924-24-3) → (2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester (864924-29-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Bu₂BOTf / diethyl ether; CH₂Cl₂ / 0.08 h / cooling

1.2: DIPEA / diethyl ether; CH₂Cl₂ / 0.75 h / 0 °C

1.3: diethyl ether; CH₂Cl₂ / 3 h / -78 - 0 °C

2.1: 318 mg / 2,6-lutidine / CH₂Cl₂ / 16 h / 20 °C

3.1: 91 percent / H₂O₂; aq. LiOH / tetrahydrofuran / 16 h / 20 °C

4.1: 1,1'-carbonyldiimidazole / dimethylformamide / 3 h / 20 °C

4.2: 83 percent / DMAP / dimethylformamide / 40 h

5.1: 94 percent / aq. HF / acetonitrile / 44 h / 0 - 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; dihydrogen peroxide; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja051430y

Reference yield:

3,5-dinitrobenzoic acid (99-34-3) → (2R,3R)-3-Hydroxy-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester (864924-29-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 86 percent / hexamethylphosphoric acid triamide / 20 h / 85 °C

2.1: 95 percent / AcOH; HBr / 20 h / Heating

3.1: 79 percent / NaBH₄; I₂ / tetrahydrofuran / 6 h / 20 °C

4.1: 75 percent / MnO₂ / CH₂Cl₂; acetone / 24 h / 20 °C

5.1: 90 percent / imidazole / dimethylformamide / 20 °C

6.1: Bu₂BOTf / diethyl ether; CH₂Cl₂ / 0.08 h / cooling

6.2: DIPEA / diethyl ether; CH₂Cl₂ / 0.75 h / 0 °C

6.3: diethyl ether; CH₂Cl₂ / 3 h / -78 - 0 °C

7.1: 318 mg / 2,6-lutidine / CH₂Cl₂ / 16 h / 20 °C

8.1: 91 percent / H₂O₂; aq. LiOH / tetrahydrofuran / 16 h / 20 °C

9.1: 1,1'-carbonyldiimidazole / dimethylformamide / 3 h / 20 °C

9.2: 83 percent / DMAP / dimethylformamide / 40 h

10.1: 94 percent / aq. HF / acetonitrile / 44 h / 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; lithium hydroxide; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; hydrogen bromide; dihydrogen peroxide; iodine; acetic acid; 1,1'-carbonyldiimidazole; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/ja051430y

upstream raw materials:

3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-benzaldehyde

(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid

(R)-4-Benzyl-3-{(2R,3R)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-3-hydroxy-2-methyl-propionyl}-oxazolidin-2-one