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

Base Information

• Chemical Name: (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid
• CAS No.: 864924-27-6
• Molecular Formula: C₁₆H₂₅NO₆Si
• Molecular Weight: 355.463
• Mol file: 864924-27-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic 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: 91.0%

4-benzyl-3-{3-(tert-butyl-dimethyl-silanyloxy)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-2-methyl-propionyl}-oxazolidin-2-one (864924-26-5) → (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid (864924-27-6)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/ja051430y

Reference yield:

4-benzyl-3-{3-(tert-butyl-dimethyl-silanyloxy)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-2-methyl-propionyl}-oxazolidin-2-one + t-butyldimethylsiyl triflate (69739-34-0) → (2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid + (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid (864924-27-6)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 16h; Title compound not separated from byproducts;

DOI:10.1021/ja051430y

Reference yield:

3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-benzaldehyde (864924-24-3) → (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid (864924-27-6)

Guidance literature:

Multi-step reaction with 3 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

With 2,6-dimethylpyridine; lithium hydroxide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja051430y

upstream raw materials:

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

t-butyldimethylsiyl triflate

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

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

Downstream raw materials:

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

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