(2Z,7S)-7-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-2-methyl-5,5-(trimethylenedithio)-2-octenal

Base Information

Chemical Name:(2Z,7S)-7-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-2-methyl-5,5-(trimethylenedithio)-2-octenal
CAS No.:156261-87-9
Molecular Formula:C₃₄H₅₂O₃S₂Si₂
Molecular Weight:629.088
Hs Code.:

Synonyms:(2Z,7S)-7-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-2-methyl-5,5-(trimethylenedithio)-2-octenal

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Chemical Property of (2Z,7S)-7-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-2-methyl-5,5-(trimethylenedithio)-2-octenal

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Technology Process of (2Z,7S)-7-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-2-methyl-5,5-(trimethylenedithio)-2-octenal

There total 9 articles about (2Z,7S)-7-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-2-methyl-5,5-(trimethylenedithio)-2-octenal 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: 92.0%

: 156261-86-8
(2Z,7S)-7-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-2-methyl-5,5-(trimethylenedithio)-2-octen-1-ol

: 156261-87-9
(2Z,7S)-7-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-2-methyl-5,5-(trimethylenedithio)-2-octenal

Guidance literature:: With manganese(IV) oxide; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1246/bcsj.66.3464

Reference yield:

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

: 156261-87-9
(2Z,7S)-7-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-2-methyl-5,5-(trimethylenedithio)-2-octenal

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 156261-87-9
(2Z,7S)-7-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-2-methyl-5,5-(trimethylenedithio)-2-octenal

Guidance literature:: Multi-step reaction with 6 steps

1: imidazole / CH₂Cl₂ / 15 h / Ambient temperature

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

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

4: 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

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

6: 92 percent / MnO₂ / CH₂Cl₂ / 2 h / Ambient temperature

With 1H-imidazole; dmap; manganese(IV) oxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; pyridinium p-toluenesulfonate; sodium t-butanolate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.66.3464