(S)-4-Benzyl-3-[(2S,3R)-3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-2-methylsulfanyl-propionyl]-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-[(2S,3R)-3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-2-methylsulfanyl-propionyl]-oxazolidin-2-one
• CAS No.: 190664-61-0
• Molecular Formula: C₂₁H₂₂ClNO₆S
• Molecular Weight: 451.928
• Mol file: 190664-61-0.mol

Synonyms:(S)-4-Benzyl-3-[(2S,3R)-3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-2-methylsulfanyl-propionyl]-oxazolidin-2-one

Chemical Property of (S)-4-Benzyl-3-[(2S,3R)-3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-2-methylsulfanyl-propionyl]-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzyl-3-[(2S,3R)-3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-2-methylsulfanyl-propionyl]-oxazolidin-2-one

There total 2 articles about (S)-4-Benzyl-3-[(2S,3R)-3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-2-methylsulfanyl-propionyl]-oxazolidin-2-one 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:

2-chloro-3-hydroxy-4-methoxybenzaldehyde (37687-57-3) → (S)-4-Benzyl-3-[(2S,3R)-3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-2-methylsulfanyl-propionyl]-oxazolidin-2-one (190664-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / K₂CO₃ / dimethylformamide / 2 h / 25 °C

2: 1.) ⁿBu₂BOTf, Et₃N / 1.) CH₂Cl₂, from -78 to 0 degC, 40 min; 2.) -78 degC, 45 min then 0 degC, 10 min

With di-n-butylboryl trifluoromethanesulfonate; potassium carbonate; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)00724-7

Reference yield:

3-benzyloxy-2-chloro-4-methoxy-benzaldehyde (53713-77-2) + (4S)-3-(Methylthioacetyl)-4-benzyl-1,3-oxazolidin-2-one (190664-60-9) → (S)-4-Benzyl-3-[(2S,3R)-3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-2-methylsulfanyl-propionyl]-oxazolidin-2-one (190664-61-0)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, from -78 to 0 degC, 40 min; 2.) -78 degC, 45 min then 0 degC, 10 min;

DOI:10.1016/S0040-4039(97)00724-7

Reference yield: 90.0%

triethylsilyl chloride (994-30-9) + (S)-4-Benzyl-3-[(2S,3R)-3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-2-methylsulfanyl-propionyl]-oxazolidin-2-one (190664-61-0) → (S)-4-Benzyl-3-[(2S,3R)-3-(2-chloro-4-methoxy-3-triethylsilanyloxy-phenyl)-2-methylsulfanyl-3-triethylsilanyloxy-propionyl]-oxazolidin-2-one (190664-62-1)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; for 1h; from 0 to 25 degC;

DOI:10.1016/S0040-4039(97)00724-7

upstream raw materials:

3-benzyloxy-2-chloro-4-methoxy-benzaldehyde

(4S)-3-(Methylthioacetyl)-4-benzyl-1,3-oxazolidin-2-one

2-chloro-3-hydroxy-4-methoxybenzaldehyde

Downstream raw materials:

(S)-4-Benzyl-3-[(2S,3R)-3-(2-chloro-4-methoxy-3-triethylsilanyloxy-phenyl)-2-methylsulfanyl-3-triethylsilanyloxy-propionyl]-oxazolidin-2-one