(E,6R,7S,10R,11R)-ethyl 11-tert-butyldiphenylsilyloxy-6-hydroxy-7,10-oxidoheneicosa-2-enoate

Base Information

Chemical Name:(E,6R,7S,10R,11R)-ethyl 11-tert-butyldiphenylsilyloxy-6-hydroxy-7,10-oxidoheneicosa-2-enoate
CAS No.:224037-48-3
Molecular Formula:C₃₉H₆₀O₅Si
Molecular Weight:636.988
Hs Code.:

Synonyms:(E,6R,7S,10R,11R)-ethyl 11-tert-butyldiphenylsilyloxy-6-hydroxy-7,10-oxidoheneicosa-2-enoate

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Chemical Property of (E,6R,7S,10R,11R)-ethyl 11-tert-butyldiphenylsilyloxy-6-hydroxy-7,10-oxidoheneicosa-2-enoate

Chemical Property:

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Technology Process of (E,6R,7S,10R,11R)-ethyl 11-tert-butyldiphenylsilyloxy-6-hydroxy-7,10-oxidoheneicosa-2-enoate

There total 11 articles about (E,6R,7S,10R,11R)-ethyl 11-tert-butyldiphenylsilyloxy-6-hydroxy-7,10-oxidoheneicosa-2-enoate 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:

: 59101-25-6
trans-pentadec-4-en-1-ol

: 224037-48-3
(E,6R,7S,10R,11R)-ethyl 11-tert-butyldiphenylsilyloxy-6-hydroxy-7,10-oxidoheneicosa-2-enoate

Guidance literature:: Multi-step reaction with 11 steps

1: 89 percent / PCC, celite / CH₂Cl₂ / 2 h

2: tetrahydrofuran / 0.5 h / 0 °C

3: propionic acid / xylene / 2 h / Heating

5: 92 percent / TsOH / acetone / 0.5 h / Ambient temperature

6: 94 percent / Et₃N / CH₂Cl₂ / 2 h / -30 - 0 °C

7: TsOH / methanol; H₂O / 16 h / Ambient temperature

8: Py / 2 h / Heating

9: 95 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

10: 2.21 g / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 °C

11: toluene / 16 h / 80 °C

With pyridine; 1H-imidazole; Celite; diisobutylaluminium hydride; toluene-4-sulfonic acid; propionic acid; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; xylene;
DOI:10.1021/jo982110i

Reference yield:

: 59101-21-2
(E)-pentadec-4-enoic acid ethyl ester

: 224037-48-3
(E,6R,7S,10R,11R)-ethyl 11-tert-butyldiphenylsilyloxy-6-hydroxy-7,10-oxidoheneicosa-2-enoate

Guidance literature:: Multi-step reaction with 12 steps

1: LiAlH₄ / diethyl ether / 1 h / 0 - 20 °C

2: 89 percent / PCC, celite / CH₂Cl₂ / 2 h

3: tetrahydrofuran / 0.5 h / 0 °C

4: propionic acid / xylene / 2 h / Heating

6: 92 percent / TsOH / acetone / 0.5 h / Ambient temperature

7: 94 percent / Et₃N / CH₂Cl₂ / 2 h / -30 - 0 °C

8: TsOH / methanol; H₂O / 16 h / Ambient temperature

9: Py / 2 h / Heating

10: 95 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

11: 2.21 g / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 °C

12: toluene / 16 h / 80 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; Celite; diisobutylaluminium hydride; toluene-4-sulfonic acid; propionic acid; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; xylene;
DOI:10.1021/jo982110i

Reference yield:

: 131618-60-5
(trans)-pentadec-4-en-1-al

: 224037-48-3
(E,6R,7S,10R,11R)-ethyl 11-tert-butyldiphenylsilyloxy-6-hydroxy-7,10-oxidoheneicosa-2-enoate

Guidance literature:: Multi-step reaction with 10 steps

1: tetrahydrofuran / 0.5 h / 0 °C

2: propionic acid / xylene / 2 h / Heating

4: 92 percent / TsOH / acetone / 0.5 h / Ambient temperature

5: 94 percent / Et₃N / CH₂Cl₂ / 2 h / -30 - 0 °C

6: TsOH / methanol; H₂O / 16 h / Ambient temperature

7: Py / 2 h / Heating

8: 95 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

9: 2.21 g / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 °C

10: toluene / 16 h / 80 °C

With pyridine; 1H-imidazole; diisobutylaluminium hydride; toluene-4-sulfonic acid; propionic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; xylene;
DOI:10.1021/jo982110i