(2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol

Base Information

Chemical Name:(2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol
CAS No.:112505-70-1
Molecular Formula:C₃₁H₅₀O₃Si
Molecular Weight:498.822
Hs Code.:

Synonyms:(2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol

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Chemical Property of (2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol

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Technology Process of (2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol

There total 12 articles about (2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol 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:

: 112505-69-8
(2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenoic acid ethyl ester

: 112505-70-1
(2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; hexane; at -70 ℃; for 0.15h;
DOI:10.1021/jo00240a032

Reference yield:

: 101376-74-3
(E)-4-(benzyloxy)-2-methylbut-2-enal

: 112505-70-1
(2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) NaH / 1.) THF, RT, 10 min, 2.) RT, 30 min

2: 88 percent / i-Bu₂AlH / diethyl ether; hexane / 0.33 h / -70 °C

3: 14.58 g / NBS, dimethyl sulfide / CH₂Cl₂ / 1 h

4: 84 percent / 0.58 h / 100 °C

5: t-BuOK / tetrahydrofuran / 0.75 h / -78 - -45 °C

6: aq. AcOH / tetrahydrofuran / 1.17 h / 60 - 65 °C

7: acetonitrile / 16 h / 80 - 85 °C

8: 70 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature

9: i-BuAlH / diethyl ether; hexane / 0.15 h / -70 °C

With 1H-imidazole; N-Bromosuccinimide; dimethylsulfide; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00240a032

Reference yield:

: 79646-66-5
(2S,3S,5S,6R)-2-methoxy-3,5-dimethyltetrahydropyran-6-methanol

: 112505-70-1
(2E,8E,10E,12E)-(4S,6S,7S)-14-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) DMSO/oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, from -60 to -30 deg C, 28 min, 2.) RT, 30 min

2: t-BuOK / tetrahydrofuran / 0.75 h / -78 - -45 °C

3: aq. AcOH / tetrahydrofuran / 1.17 h / 60 - 65 °C

4: acetonitrile / 16 h / 80 - 85 °C

5: 70 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature

6: i-BuAlH / diethyl ether; hexane / 0.15 h / -70 °C

With 1H-imidazole; oxalyl dichloride; potassium tert-butylate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00240a032