(3S,4R,5R)-2-Oxo-3-phenylsulfanyl-5-propyl-4-vinyl-tetrahydro-furan-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: (3S,4R,5R)-2-Oxo-3-phenylsulfanyl-5-propyl-4-vinyl-tetrahydro-furan-3-carboxylic acid ethyl ester
• CAS No.: 122663-81-4
• Molecular Formula: C₁₈H₂₂O₄S
• Molecular Weight: 334.436
• Mol file: 122663-81-4.mol

Synonyms:(3S,4R,5R)-2-Oxo-3-phenylsulfanyl-5-propyl-4-vinyl-tetrahydro-furan-3-carboxylic acid ethyl ester

Chemical Property of (3S,4R,5R)-2-Oxo-3-phenylsulfanyl-5-propyl-4-vinyl-tetrahydro-furan-3-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5R)-2-Oxo-3-phenylsulfanyl-5-propyl-4-vinyl-tetrahydro-furan-3-carboxylic acid ethyl ester

There total 6 articles about (3S,4R,5R)-2-Oxo-3-phenylsulfanyl-5-propyl-4-vinyl-tetrahydro-furan-3-carboxylic acid 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: 68.0%

2-Diazo-malonic acid ethyl ester (Z)-(S)-4-phenylsulfanyl-1-propyl-but-2-enyl ester (122663-85-8) → (3S,4R,5R)-2-Oxo-3-phenylsulfanyl-5-propyl-4-vinyl-tetrahydro-furan-3-carboxylic acid ethyl ester (122663-81-4)

Guidance literature:

With rhodium(II) acetate; In benzene; 1.) room temp., 10 min., 2.) 80 deg C, 20 min.;

DOI:10.1016/S0040-4039(00)99523-6

Reference yield:

phenyl propargyl sulfide (5651-88-7) → (3S,4R,5R)-2-Oxo-3-phenylsulfanyl-5-propyl-4-vinyl-tetrahydro-furan-3-carboxylic acid ethyl ester (122663-81-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) ethylmagnesium bromide / 2.) THF, 0 deg C

2: 96 percent / pyridine / tetrahydrofuran / 3 h / 0 °C

3: 83 percent / H₂ / 5percent Pd-BaSO₄ / methanol

4: 96 percent / p-toluenesulfonyl azide, triethylamine / acetonitrile / 40 h / 45 °C

5: 68 percent / rhodium acetate / benzene / 1.) room temp., 10 min., 2.) 80 deg C, 20 min.

With rhodium(II) acetate; pyridine; 4-toluenesulfonyl azide; ethylmagnesium bromide; hydrogen; triethylamine; palladium on barium sulfate; In tetrahydrofuran; methanol; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)99523-6

Reference yield:

Malonic acid ethyl ester (Z)-4-phenylsulfanyl-1-propyl-but-2-enyl ester (122663-97-2) → (3S,4R,5R)-2-Oxo-3-phenylsulfanyl-5-propyl-4-vinyl-tetrahydro-furan-3-carboxylic acid ethyl ester (122663-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / p-toluenesulfonyl azide, triethylamine / acetonitrile / 40 h / 45 °C

2: 68 percent / rhodium acetate / benzene / 1.) room temp., 10 min., 2.) 80 deg C, 20 min.

With rhodium(II) acetate; 4-toluenesulfonyl azide; triethylamine; In acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)99523-6

upstream raw materials:

2-Diazo-malonic acid ethyl ester (Z)-(S)-4-phenylsulfanyl-1-propyl-but-2-enyl ester

phenyl propargyl sulfide

1-(phenylthio)hept-2-yn-4-ol

Malonic acid ethyl ester (Z)-4-phenylsulfanyl-1-propyl-but-2-enyl ester