(2E,5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethylocta-2,6-diene-1,5-diyl diacetate

Base Information

Chemical Name:(2E,5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethylocta-2,6-diene-1,5-diyl diacetate
CAS No.:1285628-14-9
Molecular Formula:C₃₀H₄₀O₅Si
Molecular Weight:508.73
Hs Code.:

Synonyms:(2E,5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethylocta-2,6-diene-1,5-diyl diacetate

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Chemical Property of (2E,5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethylocta-2,6-diene-1,5-diyl diacetate

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Technology Process of (2E,5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethylocta-2,6-diene-1,5-diyl diacetate

There total 6 articles about (2E,5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethylocta-2,6-diene-1,5-diyl diacetate 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: 96.0%

: 1285628-10-5
(2E,4S,6E)-1-(tert-butyldiphenylsilanyloxy)-8-hydroxy-3,7-dimethylocta-2,6-dien-4-yl acetate

: 108-24-7
acetic anhydride

: 1285628-14-9
(2E,5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethylocta-2,6-diene-1,5-diyl diacetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1002/ejoc.201001315

Reference yield:

: 1068574-62-8
(2E)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-one

: 1285628-14-9
(2E,5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethylocta-2,6-diene-1,5-diyl diacetate

Guidance literature:: Multi-step reaction with 4 steps

1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / tetrahydrofuran; toluene / 36 h / -60 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 17 h / 20 °C

3: tert.-butylhydroperoxide; selenium(IV) oxide; salicylic acid / dichloromethane; water / 120 h / 0 - 20 °C

4: dmap; triethylamine / dichloromethane / 16 h / 20 °C

With tert.-butylhydroperoxide; dmap; selenium(IV) oxide; triethylamine; salicylic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; water; toluene; 3: Riley oxidation;
DOI:10.1002/ejoc.201001315

Reference yield:

: 1068574-72-0
(2E,4S)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-ol

: 1285628-14-9
(2E,5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethylocta-2,6-diene-1,5-diyl diacetate

Guidance literature:: Multi-step reaction with 3 steps

1: dmap; triethylamine / dichloromethane / 17 h / 20 °C

2: tert.-butylhydroperoxide; selenium(IV) oxide; salicylic acid / dichloromethane; water / 120 h / 0 - 20 °C

3: dmap; triethylamine / dichloromethane / 16 h / 20 °C

With tert.-butylhydroperoxide; dmap; selenium(IV) oxide; triethylamine; salicylic acid; In dichloromethane; water; 2: Riley oxidation;
DOI:10.1002/ejoc.201001315