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

Base Information

• Chemical Name: (Z)-7-[(1S,2R,3R,5S)-3-Acetoxy-5-hydroxy-2-((E)-(S)-1-phenylsulfanyl-oct-2-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester
• CAS No.: 214748-72-8
• Molecular Formula: C₃₀H₄₄O₅S
• Molecular Weight: 516.742
• Mol file: 214748-72-8.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (Z)-7-[(1S,2R,3R,5S)-3-Acetoxy-5-hydroxy-2-((E)-(S)-1-phenylsulfanyl-oct-2-enyl)-cyclopentyl]-hept-5-enoic 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: 42.0%

vinyl acetate (108-05-4,9003-20-7) + (Z)-7-[(1S,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-1-phenylsulfanyl-oct-2-enyl)-cyclopentyl]-hept-5-enoic 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 (214748-71-7) + (Z)-7-[(1S,2R,3R,5S)-3-Acetoxy-5-hydroxy-2-((E)-(S)-1-phenylsulfanyl-oct-2-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester (214748-72-8)

Guidance literature:

With Amano lopase AK; for 120h;

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-[(1S,2R,3R,5S)-3-Acetoxy-5-hydroxy-2-((E)-(S)-1-phenylsulfanyl-oct-2-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester (214748-72-8)

Guidance literature:

Multi-step reaction with 5 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: 42 percent / Amano lopase AK / 120 h

With sodium tetrahydroborate; Amano lopase AK; Rh₂(Oct)4; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; dichloromethane;

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

Reference yield:

(Z)-7-[(1R,4S,5S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-hept-1-enyl)-2-oxo-bicyclo[3.1.0]hex-1-yl]-hept-5-enoic acid ethyl ester → (Z)-7-[(1S,2R,3R,5S)-3-Acetoxy-5-hydroxy-2-((E)-(S)-1-phenylsulfanyl-oct-2-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester (214748-72-8)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 32 percent / NaBH₄ / methanol / 1 h / 0 °C

3: 93 percent / n-Bu₄NF / tetrahydrofuran / 24 h / 0 °C

4: 42 percent / Amano lopase AK / 120 h

With sodium tetrahydroborate; Amano lopase AK; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; dichloromethane;

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

upstream raw materials:

vinyl acetate

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