(3,5-dimethoxy-phenyl)-acetic acid 3-acetoxy-5-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-4-methylsulfanyl-5-oxo-pentyl ester

Base Information

• Chemical Name: (3,5-dimethoxy-phenyl)-acetic acid 3-acetoxy-5-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-4-methylsulfanyl-5-oxo-pentyl ester
• CAS No.: 935658-30-3
• Molecular Formula: C₂₉H₃₅NO₉S
• Molecular Weight: 573.664
• Mol file: 935658-30-3.mol

Synonyms:(3,5-dimethoxy-phenyl)-acetic acid 3-acetoxy-5-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-4-methylsulfanyl-5-oxo-pentyl ester

Chemical Property of (3,5-dimethoxy-phenyl)-acetic acid 3-acetoxy-5-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-4-methylsulfanyl-5-oxo-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3,5-dimethoxy-phenyl)-acetic acid 3-acetoxy-5-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-4-methylsulfanyl-5-oxo-pentyl ester

There total 4 articles about (3,5-dimethoxy-phenyl)-acetic acid 3-acetoxy-5-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-4-methylsulfanyl-5-oxo-pentyl 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:

(R)-1-formylpropan-2-yl 2-(3,5-dimethoxyphenyl)acetate (935658-21-2) + acetic anhydride (108-24-7) + (4S)-3-(Methylthioacetyl)-4-benzyl-1,3-oxazolidin-2-one (190664-60-9) → (3,5-dimethoxy-phenyl)-acetic acid 3-acetoxy-5-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-4-methylsulfanyl-5-oxo-pentyl ester + (3,5-dimethoxy-phenyl)-acetic acid 3-acetoxy-5-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-4-methylsulfanyl-5-oxo-pentyl ester (935658-30-3)

Guidance literature:

(4S)-3-(Methylthioacetyl)-4-benzyl-1,3-oxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃; for 1h;

(R)-1-formylpropan-2-yl 2-(3,5-dimethoxyphenyl)acetate; In dichloromethane; at -78 - 0 ℃;

acetic anhydride; With pyridine; at 20 ℃; for 5h;

DOI:10.1021/jo070159v

Reference yield:

(R)-1-(1,3-dithian-2-yl)propan-2-yl 2-(3,5-dimethoxyphenyl)acetate (935658-20-1) → (3,5-dimethoxy-phenyl)-acetic acid 3-acetoxy-5-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-4-methylsulfanyl-5-oxo-pentyl ester (935658-30-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / PbO₂; BF₃*Et₂O / tetrahydrofuran; H₂O / 20 °C

2.1: dibutylboryl triflate; triethylamine / CH₂Cl₂ / 1 h / 0 °C

2.2: CH₂Cl₂ / -78 - 0 °C

2.3: 5.58 g / pyridine / 5 h / 20 °C

With di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; lead dioxide; triethylamine; In tetrahydrofuran; dichloromethane; water; 2.2: Evans aldol reaction;

DOI:10.1021/jo070159v

Reference yield:

(3,5-dimethoxyphenyl)acetic acid (4670-10-4) → (3,5-dimethoxy-phenyl)-acetic acid 3-acetoxy-5-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-4-methylsulfanyl-5-oxo-pentyl ester (935658-30-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / DCC; DMAP / diethyl ether / 3 h / 20 °C

2.1: 86 percent / PbO₂; BF₃*Et₂O / tetrahydrofuran; H₂O / 20 °C

3.1: dibutylboryl triflate; triethylamine / CH₂Cl₂ / 1 h / 0 °C

3.2: CH₂Cl₂ / -78 - 0 °C

3.3: 5.58 g / pyridine / 5 h / 20 °C

With dmap; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; lead dioxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; water; 3.2: Evans aldol reaction;

DOI:10.1021/jo070159v

upstream raw materials:

(R)-1-formylpropan-2-yl 2-(3,5-dimethoxyphenyl)acetate

acetic anhydride

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

(R)-1-(1,3-dithian-2-yl)propan-2-yl 2-(3,5-dimethoxyphenyl)acetate

Downstream raw materials:

3-acetoxy-5-[(3,5-dimethoxy-phenyl)-acetoxy]-hexanoic acid

(3,5-dimethoxy-phenyl)-acetic acid 3-acetoxy-5-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-methyl-5-oxo-pentyl ester