(3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-oct-7-ene

Base Information

Chemical Name:(3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-oct-7-ene
CAS No.:1274953-81-9
Molecular Formula:C₂₈H₅₂O₄Si₂
Molecular Weight:508.889
Hs Code.:

Synonyms:(3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-oct-7-ene

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Chemical Property of (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-oct-7-ene

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Technology Process of (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-oct-7-ene

There total 5 articles about (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-oct-7-ene 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: 86.0%

: 1274953-79-5
(3S,5S)-1-(4-methoxy-benzyloxy)-oct-7-ene-3,5-diol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1274953-81-9
(3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-oct-7-ene

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; Inert atmosphere;
DOI:10.1021/ol2003836

Reference yield:

: 1208329-03-6
(S,E)-8-(4-methoxy-benzyloxy)-octa-1,5-dien-4-ol

: 1274953-81-9
(3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-oct-7-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: titanium(IV) isopropylate; (-)-diethyl tartrate / dichloromethane / 0.75 h / -20 °C / Inert atmosphere

1.2: 7 h / -20 °C / Inert atmosphere

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; methanol; toluene / 18.17 h / 0 - 23 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; (-)-diethyl tartrate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Sharpless epoxidation / 1.2: Sharpless epoxidation;
DOI:10.1021/ol2003836

Reference yield:

: 1274953-78-4
(S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol

: 1274953-81-9
(3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-oct-7-ene

Guidance literature:: Multi-step reaction with 2 steps

1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; methanol; toluene / 18.17 h / 0 - 23 °C / Inert atmosphere

2: 1H-imidazole / N,N-dimethyl-formamide / Inert atmosphere

With 1H-imidazole; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol2003836