(2E,4S)-1-[(tert-butyldiphenylsilanyl)oxy]-7-hydroxy-3,7-dimethyloct-2-en-4-yl acetate

Base Information

Chemical Name:(2E,4S)-1-[(tert-butyldiphenylsilanyl)oxy]-7-hydroxy-3,7-dimethyloct-2-en-4-yl acetate
CAS No.:1285628-28-5
Molecular Formula:C₂₈H₄₀O₄Si
Molecular Weight:468.709
Hs Code.:

Synonyms:(2E,4S)-1-[(tert-butyldiphenylsilanyl)oxy]-7-hydroxy-3,7-dimethyloct-2-en-4-yl acetate

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Chemical Property of (2E,4S)-1-[(tert-butyldiphenylsilanyl)oxy]-7-hydroxy-3,7-dimethyloct-2-en-4-yl acetate

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Technology Process of (2E,4S)-1-[(tert-butyldiphenylsilanyl)oxy]-7-hydroxy-3,7-dimethyloct-2-en-4-yl acetate

There total 4 articles about (2E,4S)-1-[(tert-butyldiphenylsilanyl)oxy]-7-hydroxy-3,7-dimethyloct-2-en-4-yl acetate 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: 88.0%

: 1285628-23-0
(5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethyloct-6-ene-2,5-diol

: 108-24-7
acetic anhydride

: 1285628-28-5
(2E,4S)-1-[(tert-butyldiphenylsilanyl)oxy]-7-hydroxy-3,7-dimethyloct-2-en-4-yl acetate

: 1285628-29-6
C₃₀H₄₂O₅Si

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1002/ejoc.201001315

Reference yield:

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

: 1285628-28-5
(2E,4S)-1-[(tert-butyldiphenylsilanyl)oxy]-7-hydroxy-3,7-dimethyloct-2-en-4-yl acetate

: 1285628-29-6
C₃₀H₄₂O₅Si

Guidance literature:: Multi-step reaction with 5 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: 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 3 h / 0 °C

4: lithium triethylborohydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere; Reflux

5: dmap; triethylamine / dichloromethane / 15 h / 20 °C

With dmap; lithium triethylborohydride; triethylamine; 3-chloro-benzenecarboperoxoic 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;
DOI:10.1002/ejoc.201001315

Reference yield:

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

: 1285628-28-5
(2E,4S)-1-[(tert-butyldiphenylsilanyl)oxy]-7-hydroxy-3,7-dimethyloct-2-en-4-yl acetate

: 1285628-29-6
C₃₀H₄₂O₅Si

Guidance literature:: Multi-step reaction with 4 steps

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

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 3 h / 0 °C

3: lithium triethylborohydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere; Reflux

4: dmap; triethylamine / dichloromethane / 15 h / 20 °C

With dmap; lithium triethylborohydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1002/ejoc.201001315