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

Base Information

Chemical Name:7-{(1S,5R)-5-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-heptanoic acid methyl ester
CAS No.:251292-83-8
Molecular Formula:C₃₇H₅₂O₄Si
Molecular Weight:588.903
Hs Code.:

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

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

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

There total 8 articles about 7-{(1S,5R)-5-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-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: 82.0%

: 251292-82-7
7-{(1R,2R,5S)-5-Acetoxy-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-3-oxo-cyclopentyl}-heptanoic acid methyl ester

: 251292-83-8
7-{(1S,5R)-5-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-heptanoic acid methyl ester

Guidance literature:: With sodium hydrogencarbonate; In methanol; at 20 ℃;
DOI:10.1039/a903813b

Reference yield:

: 61305-35-9
(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone

: 251292-83-8
7-{(1S,5R)-5-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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

6: 79 percent / CH₃COOH; H₂O / tetrahydrofuran / 48 h / 20 °C

7: 89 percent / Dess-Martin reagent / CH₂Cl₂ / 20 °C

8: 82 percent / NaHCO₃ / methanol / 20 °C

With pyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; Schwartz's reagent; water; methyllithium; L-Selectride; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; acetic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Iodination / 2: Addition / 3: Addition / 4: Reduction / 5: Acetylation / 6: Hydrolysis / 7: Oxidation / 8: Elimination;
DOI:10.1039/a903813b

Reference yield:

: 150686-70-7
(R)-4-((tert-butyldimethylsilyl)oxy)-2-iodocyclopent-2-en-1-one

: 251292-83-8
7-{(1S,5R)-5-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 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

5: 79 percent / CH₃COOH; H₂O / tetrahydrofuran / 48 h / 20 °C

6: 89 percent / Dess-Martin reagent / CH₂Cl₂ / 20 °C

7: 82 percent / NaHCO₃ / methanol / 20 °C

With pyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; Schwartz's reagent; water; methyllithium; L-Selectride; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; acetic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Addition / 2: Addition / 3: Reduction / 4: Acetylation / 5: Hydrolysis / 6: Oxidation / 7: Elimination;
DOI:10.1039/a903813b