ethyl 6(S)-(benzoyloxy)-13(R)-<(tert-butyldiphenylsilyl)oxy>-7(Z),9(E),11(E),15(Z)-henicosatetraenoate

Base Information

• Chemical Name: ethyl 6(S)-(benzoyloxy)-13(R)-<(tert-butyldiphenylsilyl)oxy>-7(Z),9(E),11(E),15(Z)-henicosatetraenoate
• CAS No.: 119392-39-1
• Molecular Formula: C₄₆H₆₀O₅Si
• Molecular Weight: 721.065
• Mol file: 119392-39-1.mol

Synonyms:ethyl 6(S)-(benzoyloxy)-13(R)-<(tert-butyldiphenylsilyl)oxy>-7(Z),9(E),11(E),15(Z)-henicosatetraenoate

Chemical Property of ethyl 6(S)-(benzoyloxy)-13(R)-<(tert-butyldiphenylsilyl)oxy>-7(Z),9(E),11(E),15(Z)-henicosatetraenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6(S)-(benzoyloxy)-13(R)-<(tert-butyldiphenylsilyl)oxy>-7(Z),9(E),11(E),15(Z)-henicosatetraenoate

There total 26 articles about ethyl 6(S)-(benzoyloxy)-13(R)-<(tert-butyldiphenylsilyl)oxy>-7(Z),9(E),11(E),15(Z)-henicosatetraenoate 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:

tert-butylchlorodiphenylsilane (58479-61-1) → ethyl 6(S)-(benzoyloxy)-13(R)-<(tert-butyldiphenylsilyl)oxy>-7(Z),9(E),11(E),15(Z)-henicosatetraenoate (119392-39-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / dimethylformamide / 22 h / 65 °C

2: 100 percent / aluminum hydride / tetrahydrofuran / 2.5 h / 0 °C

3: 90 percent / CBr₄, ethylenebis(diphenylphosphine) / CH₂Cl₂ / 2.5 h / -35 °C

4: 153 mg / acetonitrile / 1.5 h / 20 °C

5: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -100 deg C, 2 min, 2.) THF, hexane, from -100 deg C to RT

With aluminium hydride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; carbon tetrabromide; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00271a032

Reference yield:

1-Heptyne (628-71-7) → ethyl 6(S)-(benzoyloxy)-13(R)-<(tert-butyldiphenylsilyl)oxy>-7(Z),9(E),11(E),15(Z)-henicosatetraenoate (119392-39-1)

Guidance literature:

Multi-step reaction with 12 steps

2: 98 percent / hydrogen / Lindlar catalyst / benzene / Ambient temperature

3: 90 percent / 90percent aqueous CF₃COOH / 3 h / 0 °C

4: 65 percent / lead tetraacetate / benzene / 1 h / Ambient temperature

5: 50 percent / benzene / 4 h / Heating

6: NaH / 1.) benzene, RT, 1 h, 2.) benzene, RT, 4 h

7: 80 percent / potassium carbonate / ethanol / 22 h / 45 °C

8: 85 percent / dimethylformamide / 22 h / 65 °C

9: 100 percent / aluminum hydride / tetrahydrofuran / 2.5 h / 0 °C

10: 90 percent / CBr₄, ethylenebis(diphenylphosphine) / CH₂Cl₂ / 2.5 h / -35 °C

11: 153 mg / acetonitrile / 1.5 h / 20 °C

12: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -100 deg C, 2 min, 2.) THF, hexane, from -100 deg C to RT

With aluminium hydride; lead(IV) acetate; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; carbon tetrabromide; hydrogen; sodium hydride; potassium carbonate; trifluoroacetic acid; 1,2-bis-(diphenylphosphino)ethane; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo00271a032

Reference yield:

(4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol (212579-64-1) → ethyl 6(S)-(benzoyloxy)-13(R)-<(tert-butyldiphenylsilyl)oxy>-7(Z),9(E),11(E),15(Z)-henicosatetraenoate (119392-39-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 84 percent / propanoic acid / 2.5 h / 137 °C

2: 90 percent / hydrogen / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature

3: 66 percent / 10percent aq. H₂SO₄ / ethanol / 4 h / 0 °C

4: 100 percent / imidazole / dimethylformamide / 4 h / 20 °C

5: 1.47 g / pyridine / 3 h / 0 °C

6: 85 percent / 90percent aq. CF₃COOH / 2 h / 0 °C

7: 93 percent / CF₃COOH, pyridine, N,N'-dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 2.5 h / Ambient temperature

8: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -100 deg C, 2 min, 2.) THF, hexane, from -100 deg C to RT

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sulfuric acid; hydrogen; propionic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00271a032

upstream raw materials:

<6(R)-<(tert-butyldiphenylsilyl)oxy>-2(E),4(E),8(Z)-tetradecatrien-1-yl>triphenylphosphonium bromide

ethyl 6(S)-(benzoyloxy)-6-formylhexanoate

1-Heptyne

ethyl 6(S)-(benzoyloxy)-7-hydroxyheptanoate

Refernces