(5E,7R,8Z,13S)-13-(t-butyldimethylsilyloxy)-14-(t-butyldiphenylsilyloxy)-1-(4,4'-dimethoxytriphenylmethoxy)-6,8-dimethyl-11,11-(trimethylenedithio)-5,8-tetradecadien-7-ol

Base Information

Chemical Name:(5E,7R,8Z,13S)-13-(t-butyldimethylsilyloxy)-14-(t-butyldiphenylsilyloxy)-1-(4,4'-dimethoxytriphenylmethoxy)-6,8-dimethyl-11,11-(trimethylenedithio)-5,8-tetradecadien-7-ol
CAS No.:156261-90-4
Molecular Formula:C₆₂H₈₄O₆S₂Si₂
Molecular Weight:1045.65
Hs Code.:

(5E,7R,8Z,13S)-13-(t-butyldimethylsilyloxy)-14-(t-butyldiphenylsilyloxy)-1-(4,4'-dimethoxytriphenylmethoxy)-6,8-dimethyl-11,11-(trimethylenedithio)-5,8-tetradecadien-7-ol

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Chemical Property of (5E,7R,8Z,13S)-13-(t-butyldimethylsilyloxy)-14-(t-butyldiphenylsilyloxy)-1-(4,4'-dimethoxytriphenylmethoxy)-6,8-dimethyl-11,11-(trimethylenedithio)-5,8-tetradecadien-7-ol

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Technology Process of (5E,7R,8Z,13S)-13-(t-butyldimethylsilyloxy)-14-(t-butyldiphenylsilyloxy)-1-(4,4'-dimethoxytriphenylmethoxy)-6,8-dimethyl-11,11-(trimethylenedithio)-5,8-tetradecadien-7-ol

There total 15 articles about (5E,7R,8Z,13S)-13-(t-butyldimethylsilyloxy)-14-(t-butyldiphenylsilyloxy)-1-(4,4'-dimethoxytriphenylmethoxy)-6,8-dimethyl-11,11-(trimethylenedithio)-5,8-tetradecadien-7-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:

: 928-90-5
5-hexyl-1-ol

: 156261-90-4
(5E,7R,8Z,13S)-13-(t-butyldimethylsilyloxy)-14-(t-butyldiphenylsilyloxy)-1-(4,4'-dimethoxytriphenylmethoxy)-6,8-dimethyl-11,11-(trimethylenedithio)-5,8-tetradecadien-7-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) TMEDA, n-BuLi / 1.) THF, hexane, -50 deg C, 45 min 2.) THF, hexane, from -50 deg C to -10 deg C, 2 h

2: 1.) DIBAL, 2.) MeLi

3: Br₂ / CH₂Cl₂ / 1 h / -78 °C

4: 4.9 M NaOMe in MeOH / CH₂Cl₂ / 2.5 h / 0 - 20 °C

5: 97 percent / Et₃N / dimethylformamide / 2 h / Ambient temperature

6: 1.) t-BuLi / 1.) THF, pentane, from -90 deg C to -80 deg C, 0.5 h, 2.) THF, pentane, from -90 deg C to -40 deg C, 2 h

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; methyllithium; bromine; tert.-butyl lithium; sodium methylate; diisobutylaluminium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.66.3464

Reference yield:

: 103620-62-8
6-<(trimethylsilyl)oxy>-1-(trimethylsilyl)-1-hexyne

: 156261-90-4
(5E,7R,8Z,13S)-13-(t-butyldimethylsilyloxy)-14-(t-butyldiphenylsilyloxy)-1-(4,4'-dimethoxytriphenylmethoxy)-6,8-dimethyl-11,11-(trimethylenedithio)-5,8-tetradecadien-7-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) DIBAL, 2.) MeLi

2: Br₂ / CH₂Cl₂ / 1 h / -78 °C

3: 4.9 M NaOMe in MeOH / CH₂Cl₂ / 2.5 h / 0 - 20 °C

4: 97 percent / Et₃N / dimethylformamide / 2 h / Ambient temperature

5: 1.) t-BuLi / 1.) THF, pentane, from -90 deg C to -80 deg C, 0.5 h, 2.) THF, pentane, from -90 deg C to -40 deg C, 2 h

With methyllithium; bromine; tert.-butyl lithium; sodium methylate; diisobutylaluminium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.66.3464

Reference yield:

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

: 156261-90-4
(5E,7R,8Z,13S)-13-(t-butyldimethylsilyloxy)-14-(t-butyldiphenylsilyloxy)-1-(4,4'-dimethoxytriphenylmethoxy)-6,8-dimethyl-11,11-(trimethylenedithio)-5,8-tetradecadien-7-ol

Guidance literature:: Multi-step reaction with 6 steps

1: n-BuLi, TMEDA / tetrahydrofuran / 1.) -30 deg C, 1.5 h, 2.) room temp., 15 h

2: DMAP / dimethylformamide / 15 h / 50 °C

3: 1.) n-BuLi, t-BuONa / 1.) hexane, THF, -78 deg C, 1 h, 2.) hexane, THF, from -85 deg C to -55 deg C, 1 h

4: PPTS / CH₂Cl₂; methanol / 2 h / Ambient temperature

5: 92 percent / MnO₂ / CH₂Cl₂ / 2 h / Ambient temperature

6: 1.) t-BuLi / 1.) THF, pentane, from -90 deg C to -80 deg C, 0.5 h, 2.) THF, pentane, from -90 deg C to -40 deg C, 2 h

With dmap; manganese(IV) oxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium t-butanolate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.66.3464