(3S,6R,9R,E)-9-(tert-butyldiphenylsilyloxy)-3,6-bis(methoxymethoxy)octadec-4-enoic acid

Base Information

Chemical Name:(3S,6R,9R,E)-9-(tert-butyldiphenylsilyloxy)-3,6-bis(methoxymethoxy)octadec-4-enoic acid
CAS No.:1615198-71-4
Molecular Formula:C₃₈H₆₀O₇Si
Molecular Weight:656.976
Hs Code.:

Synonyms:(3S,6R,9R,E)-9-(tert-butyldiphenylsilyloxy)-3,6-bis(methoxymethoxy)octadec-4-enoic acid

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Chemical Property of (3S,6R,9R,E)-9-(tert-butyldiphenylsilyloxy)-3,6-bis(methoxymethoxy)octadec-4-enoic acid

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Technology Process of (3S,6R,9R,E)-9-(tert-butyldiphenylsilyloxy)-3,6-bis(methoxymethoxy)octadec-4-enoic acid

There total 12 articles about (3S,6R,9R,E)-9-(tert-butyldiphenylsilyloxy)-3,6-bis(methoxymethoxy)octadec-4-enoic acid 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: 85.0%

: 1615198-70-3
(3S,6R,9R,E)-9-(tert-butyldiphenylsilyloxy)-3,6-bis(methoxymethoxy)octadec-4-en-1-ol

: 1615198-71-4
(3S,6R,9R,E)-9-(tert-butyldiphenylsilyloxy)-3,6-bis(methoxymethoxy)octadec-4-enoic acid

Guidance literature:: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In water; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tet.2014.05.021

Reference yield:

: 99493-58-0
(4R)-tridec-1-en-4-ol

: 1615198-71-4
(3S,6R,9R,E)-9-(tert-butyldiphenylsilyloxy)-3,6-bis(methoxymethoxy)octadec-4-enoic acid

Guidance literature:: Multi-step reaction with 9 steps

1: dmap; 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

2: dimethyl sulfide borane / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 3 h / 20 °C / Inert atmosphere

4: dmap; triethylamine; N,O-dimethylhydroxylamine*hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 6 h / 20 °C / Inert atmosphere

5: vinyl magnesium bromide / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

6: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethyl sulfide borane / tetrahydrofuran; toluene / 6 h / -78 °C / Inert atmosphere

7: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 12 h / 20 °C / Inert atmosphere

8: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Reflux; Inert atmosphere

9: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; Hoveyda-Grubbs catalyst second generation; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; vinyl magnesium bromide; N,O-dimethylhydroxylamine*hydrochloride; dimethyl sulfide borane; tetra-(n-butyl)ammonium iodide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2014.05.021

Reference yield:

: 1615198-56-5
(S)-1-methoxy-4-((3-(methoxymethoxy)pent-4-enyloxy)methyl)benzene

: 1615198-71-4
(3S,6R,9R,E)-9-(tert-butyldiphenylsilyloxy)-3,6-bis(methoxymethoxy)octadec-4-enoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; aq. phosphate buffer / 1 h / 20 °C / pH 7 / Inert atmosphere

2: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Reflux; Inert atmosphere

3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water / 2 h / 20 °C / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In aq. phosphate buffer; dichloromethane; water;
DOI:10.1016/j.tet.2014.05.021