(2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienal

Base Information

Chemical Name:(2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienal
CAS No.:185909-42-6
Molecular Formula:C₂₈H₄₄O₅Si
Molecular Weight:488.74
Hs Code.:

Synonyms:(2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienal

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Chemical Property of (2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienal

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Technology Process of (2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienal

There total 13 articles about (2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienal 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: 98.0%

: 185909-59-5
(2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trien-1-ol

: 185909-42-6
(2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienal

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 23 ℃;
DOI:10.1016/S0040-4039(96)02110-7

Reference yield:

: 185909-45-9
(S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyraldehyde

: 185909-42-6
(2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienal

Guidance literature:: Multi-step reaction with 11 steps

1: 79 percent / Ti(OiPr)4, (S)-BINOL / CH₂Cl₂ / 144 h / -20 °C

2: 96 percent / NaH / dimethylformamide

3: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C

4: 75 percent / KN(TMS)2, 18-crown-6 / tetrahydrofuran / -78 °C

5: Et₃N-HF / acetonitrile

6: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 °C

7: 78 percent / CrCl₂ / dioxane; tetrahydrofuran

8: 83 percent / Pd(PPh₃)4, TlOH / tetrahydrofuran; H₂O / 2 h

9: 99 percent / imidazole / dimethylformamide

10: 87 percent / DIBAL-H / CH₂Cl₂ / -78 °C

11: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 23 °C

With 1H-imidazole; chromium dichloride; titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; oxalyl dichloride; 18-crown-6 ether; (S)-[1,1']-binaphthalenyl-2,2'-diol; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine hydrofluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(96)02110-7

Reference yield:

: (S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butan-1-ol

: 185909-42-6
(2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienal

Guidance literature:: Multi-step reaction with 12 steps

1: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

2: 79 percent / Ti(OiPr)4, (S)-BINOL / CH₂Cl₂ / 144 h / -20 °C

3: 96 percent / NaH / dimethylformamide

4: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C

5: 75 percent / KN(TMS)2, 18-crown-6 / tetrahydrofuran / -78 °C

6: Et₃N-HF / acetonitrile

7: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 °C

8: 78 percent / CrCl₂ / dioxane; tetrahydrofuran

9: 83 percent / Pd(PPh₃)4, TlOH / tetrahydrofuran; H₂O / 2 h

10: 99 percent / imidazole / dimethylformamide

11: 87 percent / DIBAL-H / CH₂Cl₂ / -78 °C

12: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 23 °C

With 1H-imidazole; chromium dichloride; titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; oxalyl dichloride; 18-crown-6 ether; (S)-[1,1']-binaphthalenyl-2,2'-diol; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine hydrofluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(96)02110-7