(5Z,8Z,10E)-12-(tert-Butyl-diphenyl-silanyloxy)-15-diazo-14-oxo-icosa-5,8,10-trienoic acid ethyl ester

Base Information

Chemical Name:(5Z,8Z,10E)-12-(tert-Butyl-diphenyl-silanyloxy)-15-diazo-14-oxo-icosa-5,8,10-trienoic acid ethyl ester
CAS No.:331825-31-1
Molecular Formula:C₃₈H₅₂N₂O₄Si
Molecular Weight:628.927
Hs Code.:

Synonyms:(5Z,8Z,10E)-12-(tert-Butyl-diphenyl-silanyloxy)-15-diazo-14-oxo-icosa-5,8,10-trienoic acid ethyl ester

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Chemical Property of (5Z,8Z,10E)-12-(tert-Butyl-diphenyl-silanyloxy)-15-diazo-14-oxo-icosa-5,8,10-trienoic acid ethyl ester

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Technology Process of (5Z,8Z,10E)-12-(tert-Butyl-diphenyl-silanyloxy)-15-diazo-14-oxo-icosa-5,8,10-trienoic acid ethyl ester

There total 12 articles about (5Z,8Z,10E)-12-(tert-Butyl-diphenyl-silanyloxy)-15-diazo-14-oxo-icosa-5,8,10-trienoic acid ethyl ester 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:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 331825-37-7
(5Z,8Z,10E)-15-Diazo-12-hydroxy-14-oxo-icosa-5,8,10-trienoic acid ethyl ester

: 331825-31-1
(5Z,8Z,10E)-12-(tert-Butyl-diphenyl-silanyloxy)-15-diazo-14-oxo-icosa-5,8,10-trienoic acid ethyl ester

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/jo001731k

Reference yield:

: 542-28-9,26354-94-9
3,4,5,6-tetrahydro-2H-pyran-2-one

: 331825-31-1
(5Z,8Z,10E)-12-(tert-Butyl-diphenyl-silanyloxy)-15-diazo-14-oxo-icosa-5,8,10-trienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

2.1: PCC

3.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C

3.2: 75 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C

4.1: 91 percent / aq. AcOH / 42 h / 20 °C

5.1: NaIO₄; SiO₂ / H₂O; CH₂Cl₂ / 0.33 h / 20 °C

6.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C

6.2: 1.19 g / CH₂Cl₂ / 4 h / -78 - 20 °C

7.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / 20 °C

8.1: KHMDS / toluene / 0.17 h / -78 °C

8.2: 17.5 percent / toluene / 1 h

9.1: 2.43 g / imidazole; DMAP / CH₂Cl₂ / 12 h / 20 °C

With 1H-imidazole; dmap; sodium periodate; silica gel; potassium hexamethylsilazane; Dess-Martin periodane; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1021/jo001731k

Reference yield:

: 110-53-2
1-Bromopentane

: 331825-31-1
(5Z,8Z,10E)-12-(tert-Butyl-diphenyl-silanyloxy)-15-diazo-14-oxo-icosa-5,8,10-trienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: K₂CO₃; TBAI; Cu / toluene / 3 h / Heating

1.2: 48 percent / toluene / 43 h / 50 °C

2.1: 73 percent / DBU; p-nitrobenzenesulfonyl azide / CH₂Cl₂ / 3 h / 0 °C

3.1: KHMDS / toluene / 0.17 h / -78 °C

3.2: 17.5 percent / toluene / 1 h

4.1: 2.43 g / imidazole; DMAP / CH₂Cl₂ / 12 h / 20 °C

With 1H-imidazole; dmap; p-nitrobenzenesulfonyl azide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; copper; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene;
DOI:10.1021/jo001731k