(Z)-7-[(1R,2S,3S)-5-Oxo-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-7-[(1R,2S,3S)-5-Oxo-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl ester
• CAS No.: 214748-75-1
• Molecular Formula: C₃₃H₅₂O₄SSi
• Molecular Weight: 572.925
• Mol file: 214748-75-1.mol

Synonyms:(Z)-7-[(1R,2S,3S)-5-Oxo-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl ester

Chemical Property of (Z)-7-[(1R,2S,3S)-5-Oxo-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-[(1R,2S,3S)-5-Oxo-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl ester

There total 9 articles about (Z)-7-[(1R,2S,3S)-5-Oxo-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl 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%

(Z)-7-[(1R,2S,3S,5R)-5-Hydroxy-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl ester (214748-74-0) → (Z)-7-[(1R,2S,3S)-5-Oxo-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl ester (214748-75-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1016/S0040-4020(98)83038-X

Reference yield:

(Z)-7-[(1S,2R,3R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-2-((E)-(S)-1-phenylsulfanyl-oct-2-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester → (Z)-7-[(1R,2S,3S)-5-Oxo-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl ester (214748-75-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / n-Bu₄NF / tetrahydrofuran / 24 h / 0 °C

2: 48 percent / Amano lopase AK / 120 h

3: imidazole, 4-DMAP / CH₂Cl₂ / 0.5 h / 0 °C

4: 1.) EtOH, K₂CO₃, 2.) K₂CO₃ / 1.) 65 deg C, 1.5 h, 2.) 65 deg C, 1.5 h.

5: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / Ambient temperature

With 1H-imidazole; dmap; ethanol; Amano lopase AK; tetrabutyl ammonium fluoride; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(98)83038-X

Reference yield:

(5Z,12E,14E)-11-(tert-Butyl-diphenyl-silanyloxy)-8-diazo-9-oxo-icosa-5,12,14-trienoic acid ethyl ester → (Z)-7-[(1R,2S,3S)-5-Oxo-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl ester (214748-75-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 44 percent / Rh₂(oct)4 / CH₂Cl₂ / 0.17 h / Ambient temperature

2: 90 percent / BF₃*Et₂O / CH₂Cl₂ / 1.) -78 deg C, 10 min and -20 deg C, 1 h.

3: 32 percent / NaBH₄ / methanol / 1 h / 0 °C

4: 93 percent / n-Bu₄NF / tetrahydrofuran / 24 h / 0 °C

5: 48 percent / Amano lopase AK / 120 h

6: imidazole, 4-DMAP / CH₂Cl₂ / 0.5 h / 0 °C

7: 1.) EtOH, K₂CO₃, 2.) K₂CO₃ / 1.) 65 deg C, 1.5 h, 2.) 65 deg C, 1.5 h.

8: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / Ambient temperature

With 1H-imidazole; dmap; sodium tetrahydroborate; ethanol; Amano lopase AK; Rh₂(Oct)4; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4020(98)83038-X

upstream raw materials:

(Z)-7-[(1R,2S,3S,5R)-5-Hydroxy-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid methyl ester

(5Z,12E,14E)-8-Diazo-11-hydroxy-9-oxo-icosa-5,12,14-trienoic acid ethyl ester

(Z)-7-[(1R,2S,3S,5R)-5-Acetoxy-3-hydroxy-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester

(Z)-7-[(1R,2S,3S,5R)-5-Acetoxy-2-((E)-(R)-1-phenylsulfanyl-oct-2-enyl)-3-triethylsilanyloxy-cyclopentyl]-hept-5-enoic acid ethyl ester