methyl 5(S)-(benzoyloxy)-12(R)-(tert-butyldiphenylsiloxy)-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

Base Information

Chemical Name:methyl 5(S)-(benzoyloxy)-12(R)-(tert-butyldiphenylsiloxy)-6(Z),8(E),10(E),14(Z)-eicosatetraenoate
CAS No.:101226-20-4
Molecular Formula:C₄₄H₅₆O₅Si
Molecular Weight:693.011
Hs Code.:

Synonyms:methyl 5(S)-(benzoyloxy)-12(R)-(tert-butyldiphenylsiloxy)-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

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Chemical Property of methyl 5(S)-(benzoyloxy)-12(R)-(tert-butyldiphenylsiloxy)-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

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Technology Process of methyl 5(S)-(benzoyloxy)-12(R)-(tert-butyldiphenylsiloxy)-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

There total 21 articles about methyl 5(S)-(benzoyloxy)-12(R)-(tert-butyldiphenylsiloxy)-6(Z),8(E),10(E),14(Z)-eicosatetraenoate 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:

: 101313-12-6
2(R)-hydroxydec-4-yn-1-al diethyl acetal

: 101226-20-4
methyl 5(S)-(benzoyloxy)-12(R)-(tert-butyldiphenylsiloxy)-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / H₂, quinoline / Lindlar catalyst / ethanol / 0.67 h / 760 Torr

2: 96 percent / imidazole / tetrahydrofuran / 8 h / 25 °C

3: 78 percent / trimethylsilyl iodide, propene / CHCl₃ / 0.5 h / 25 °C

4: 90 percent / benzene / 16 h / Heating

5: 1.) NaH / 1.) benzene, 25 deg C, 1 h, 2.) benzene, 0 deg C

6: 81 percent / aluminum hydride / tetrahydrofuran / 1.5 h / 0 °C

7: 100 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1 h / 0 °C

8: 56 percent / acetonitrile / 6 h / 0 °C

9: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2a.) THF, hexane, -78 deg C, 40 min, 2b.) -20 deg C, 30 min

With 1H-imidazole; quinoline; aluminium hydride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; propene; trimethylsilyl iodide; carbon tetrabromide; hydrogen; sodium hydride; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; chloroform; acetonitrile; benzene;
DOI:10.1021/jo00358a016

Reference yield:

: 101226-15-7
2-hydroxydec-4-yn-1-al diethyl acetal

: 101226-20-4
methyl 5(S)-(benzoyloxy)-12(R)-(tert-butyldiphenylsiloxy)-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

Guidance literature:: Multi-step reaction with 11 steps

1: 87 percent / pyridine, DMAP / 25 °C

2: H₂O / 120 h / 25 °C / bacteria 4-10T (Klebsiella pneumoniae)

3: 96 percent / H₂, quinoline / Lindlar catalyst / ethanol / 0.67 h / 760 Torr

4: 96 percent / imidazole / tetrahydrofuran / 8 h / 25 °C

5: 78 percent / trimethylsilyl iodide, propene / CHCl₃ / 0.5 h / 25 °C

6: 90 percent / benzene / 16 h / Heating

7: 1.) NaH / 1.) benzene, 25 deg C, 1 h, 2.) benzene, 0 deg C

8: 81 percent / aluminum hydride / tetrahydrofuran / 1.5 h / 0 °C

9: 100 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1 h / 0 °C

10: 56 percent / acetonitrile / 6 h / 0 °C

11: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2a.) THF, hexane, -78 deg C, 40 min, 2b.) -20 deg C, 30 min

With pyridine; 1H-imidazole; quinoline; aluminium hydride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; propene; trimethylsilyl iodide; carbon tetrabromide; hydrogen; sodium hydride; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; acetonitrile; benzene;
DOI:10.1021/jo00358a016

Reference yield:

: 101226-18-0
2-acetoxydec-4-yn-1-al diethyl acetal

: 101226-20-4
methyl 5(S)-(benzoyloxy)-12(R)-(tert-butyldiphenylsiloxy)-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

Guidance literature:: Multi-step reaction with 10 steps

1: H₂O / 120 h / 25 °C / bacteria 4-10T (Klebsiella pneumoniae)

2: 96 percent / H₂, quinoline / Lindlar catalyst / ethanol / 0.67 h / 760 Torr

3: 96 percent / imidazole / tetrahydrofuran / 8 h / 25 °C

4: 78 percent / trimethylsilyl iodide, propene / CHCl₃ / 0.5 h / 25 °C

5: 90 percent / benzene / 16 h / Heating

6: 1.) NaH / 1.) benzene, 25 deg C, 1 h, 2.) benzene, 0 deg C

7: 81 percent / aluminum hydride / tetrahydrofuran / 1.5 h / 0 °C

8: 100 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1 h / 0 °C

9: 56 percent / acetonitrile / 6 h / 0 °C

10: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2a.) THF, hexane, -78 deg C, 40 min, 2b.) -20 deg C, 30 min

With 1H-imidazole; quinoline; aluminium hydride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; propene; trimethylsilyl iodide; carbon tetrabromide; hydrogen; sodium hydride; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; acetonitrile; benzene;
DOI:10.1021/jo00358a016