(3E,13E)-(7S,8R,9S,16S)-16-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-5,5,7,9-tetramethyl-oxacyclohexadeca-3,13-diene-2,6-dione

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Chemical Name:(3E,13E)-(7S,8R,9S,16S)-16-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-5,5,7,9-tetramethyl-oxacyclohexadeca-3,13-diene-2,6-dione
CAS No.:209260-22-0
Molecular Formula:C₃₆H₅₀O₅Si
Molecular Weight:590.875
Hs Code.:

Synonyms:(3E,13E)-(7S,8R,9S,16S)-16-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-5,5,7,9-tetramethyl-oxacyclohexadeca-3,13-diene-2,6-dione

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Chemical Property of (3E,13E)-(7S,8R,9S,16S)-16-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-5,5,7,9-tetramethyl-oxacyclohexadeca-3,13-diene-2,6-dione

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Technology Process of (3E,13E)-(7S,8R,9S,16S)-16-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-5,5,7,9-tetramethyl-oxacyclohexadeca-3,13-diene-2,6-dione

There total 11 articles about (3E,13E)-(7S,8R,9S,16S)-16-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-5,5,7,9-tetramethyl-oxacyclohexadeca-3,13-diene-2,6-dione 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: 79.0%

: 209260-20-8
(E)-(6S,7R,8S)-7-Hydroxy-4,4,6,8-tetramethyl-5-oxo-trideca-2,12-dienoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester

: 209260-22-0
(3E,13E)-(7S,8R,9S,16S)-16-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-5,5,7,9-tetramethyl-oxacyclohexadeca-3,13-diene-2,6-dione

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; at 25 ℃; for 12h;
DOI:10.1021/ja971109i

Reference yield:

: 106731-74-2,119944-29-5,107033-46-5
tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane

: 209260-22-0
(3E,13E)-(7S,8R,9S,16S)-16-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-5,5,7,9-tetramethyl-oxacyclohexadeca-3,13-diene-2,6-dione

Guidance literature:: Multi-step reaction with 4 steps

2: 86 percent / 4-(dimethylamino)pyridine, 1-ethyl-3-((dimethylamino)propyl)carbodiimide hydrochloride / CH₂Cl₂ / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h

3: 1) LDA / 1) THF, -78 deg C, 15 min, -40 deg c, 45 min, 2) THF, -40 deg C, 30 min

4: 79 percent / RuCl₂(=CHPh)(PCy₃)2 / CH₂Cl₂ / 12 h / 25 °C

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; Grubbs catalyst first generation; In dichloromethane;
DOI:10.1021/ja971109i

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 209260-22-0
(3E,13E)-(7S,8R,9S,16S)-16-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-5,5,7,9-tetramethyl-oxacyclohexadeca-3,13-diene-2,6-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / imidazole / dimethylformamide / 1) 0 deg C, 30 min, 2) 25 deg C, 1 h

3: 86 percent / 4-(dimethylamino)pyridine, 1-ethyl-3-((dimethylamino)propyl)carbodiimide hydrochloride / CH₂Cl₂ / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h

4: 1) LDA / 1) THF, -78 deg C, 15 min, -40 deg c, 45 min, 2) THF, -40 deg C, 30 min

5: 79 percent / RuCl₂(=CHPh)(PCy₃)2 / CH₂Cl₂ / 12 h / 25 °C

With 1H-imidazole; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; Grubbs catalyst first generation; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja971109i