ethyl (6S,7E,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxyoctadecenoate

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Chemical Name:ethyl (6S,7E,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxyoctadecenoate
CAS No.:1312759-18-4
Molecular Formula:C₅₂H₇₄O₅Si₂
Molecular Weight:835.328
Hs Code.:

Synonyms:ethyl (6S,7E,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxyoctadecenoate

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Chemical Property of ethyl (6S,7E,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxyoctadecenoate

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Technology Process of ethyl (6S,7E,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxyoctadecenoate

There total 13 articles about ethyl (6S,7E,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxyoctadecenoate 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: 63.0%

: 1312759-13-9
ethyl (6S)-6-tert-butyldiphenylsilyloxyoct-7-enoate

: 1312759-17-3
(3R,4S)-4-tert-butyldiphenylsilyloxydodec-1-en-3-ol

: 1312759-18-4
ethyl (6S,7E,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxyoctadecenoate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 25 ℃; for 22h; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.02.008

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1312759-18-4
ethyl (6S,7E,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxyoctadecenoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 1H-imidazole; dmap / dichloromethane / 10 h / -30 - 25 °C / Inert atmosphere

2.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

2.2: 15 h / 0 - 25 °C

3.1: sodium acetate; pyridinium chlorochromate / dichloromethane / 3 h / 0 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran / 0.25 h / Inert atmosphere

4.2: 18 h / 0 - 25 °C / Inert atmosphere

5.1: palladium 10% on activated carbon; hydrogen / ethanol / 22 h / 25 °C

6.1: water; trifluoroacetic acid / dichloromethane / 27 h / 0 - 25 °C

7.1: pyridine / 24 h / 0 - 25 °C / Inert atmosphere

8.1: sodium iodide; zinc / N,N-dimethyl-formamide / 8 h / 90 °C / Inert atmosphere

9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 22 h / 25 °C / Inert atmosphere

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; dimethylsulfide borane complex; palladium 10% on activated carbon; water; hydrogen; sodium acetate; sodium hydride; pyridinium chlorochromate; trifluoroacetic acid; sodium iodide; zinc; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetasy.2011.02.008

Reference yield:

: 1312759-08-2
(4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-(cyclohexylidenedioxy)hexan-1-ol

: 1312759-18-4
ethyl (6S,7E,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxyoctadecenoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium acetate; pyridinium chlorochromate / dichloromethane / 3 h / 0 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / Inert atmosphere

2.2: 18 h / 0 - 25 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / ethanol / 22 h / 25 °C

4.1: water; trifluoroacetic acid / dichloromethane / 27 h / 0 - 25 °C

5.1: pyridine / 24 h / 0 - 25 °C / Inert atmosphere

6.1: sodium iodide; zinc / N,N-dimethyl-formamide / 8 h / 90 °C / Inert atmosphere

7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 22 h / 25 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium 10% on activated carbon; water; hydrogen; sodium acetate; sodium hydride; pyridinium chlorochromate; trifluoroacetic acid; sodium iodide; zinc; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetasy.2011.02.008