7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-heptanoic acid methyl ester

Base Information

• Chemical Name: 7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-heptanoic acid methyl ester
• CAS No.: 251292-80-5
• Molecular Formula: C₄₅H₇₂O₆Si₂
• Molecular Weight: 765.234
• Mol file: 251292-80-5.mol

Synonyms:7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-heptanoic acid methyl ester

Chemical Property of 7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-heptanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-heptanoic acid methyl ester

There total 6 articles about 7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-heptanoic 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: 92.0%

acetic anhydride (108-24-7) + 7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester (251292-77-0) → 7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-heptanoic acid methyl ester (251292-80-5)

Guidance literature:

With pyridine; dmap;

DOI:10.1039/a903813b

Reference yield:

methyl hept-6-enoate (1745-17-1) → 7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-heptanoic acid methyl ester (251292-80-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / 9-BBN; Cs₂CO₃; H₂O / (dppf)PdCl₂ / tetrahydrofuran; dimethylformamide / 0 °C

2: 73 percent / Cp₂Zr(H)Cl; MeLi; CuCN / tetrahydrofuran; diethyl ether / -78 °C

3: 85 percent / L-Selectride / tetrahydrofuran / -78 °C

4: 92 percent / DMAP; pyridine

With pyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; Schwartz's reagent; water; methyllithium; L-Selectride; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; 1: Addition / 2: Addition / 3: Reduction / 4: Acetylation;

DOI:10.1039/a903813b

Reference yield:

(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone (61305-35-9) → 7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-heptanoic acid methyl ester (251292-80-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / pyridine / CH₂Cl₂ / 0 °C

2: 74 percent / 9-BBN; Cs₂CO₃; H₂O / (dppf)PdCl₂ / tetrahydrofuran; dimethylformamide / 0 °C

3: 73 percent / Cp₂Zr(H)Cl; MeLi; CuCN / tetrahydrofuran; diethyl ether / -78 °C

4: 85 percent / L-Selectride / tetrahydrofuran / -78 °C

5: 92 percent / DMAP; pyridine

With pyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; Schwartz's reagent; water; methyllithium; L-Selectride; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Iodination / 2: Addition / 3: Addition / 4: Reduction / 5: Acetylation;

DOI:10.1039/a903813b

upstream raw materials:

acetic anhydride

7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester

methyl hept-6-enoate

7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester

Downstream raw materials:

7-{(1R,2R,5S)-5-Acetoxy-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-3-oxo-cyclopentyl}-heptanoic acid methyl ester

7-{(1S,5R)-5-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-heptanoic acid methyl ester

7-{(1R,2R,3R,5S)-5-Acetoxy-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-3-hydroxy-cyclopentyl}-heptanoic acid methyl ester