(2S,3E)-5-[(tert-butyldiphenylsilanyl)oxy]-1-(3,3-dimethyloxiran-2-yl)-3-methylpent-3-en-2-yl acetate

Base Information

Chemical Name:(2S,3E)-5-[(tert-butyldiphenylsilanyl)oxy]-1-(3,3-dimethyloxiran-2-yl)-3-methylpent-3-en-2-yl acetate
CAS No.:1285628-22-9
Molecular Formula:C₂₈H₃₈O₄Si
Molecular Weight:466.693
Hs Code.:

Synonyms:(2S,3E)-5-[(tert-butyldiphenylsilanyl)oxy]-1-(3,3-dimethyloxiran-2-yl)-3-methylpent-3-en-2-yl acetate

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Chemical Property of (2S,3E)-5-[(tert-butyldiphenylsilanyl)oxy]-1-(3,3-dimethyloxiran-2-yl)-3-methylpent-3-en-2-yl acetate

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Technology Process of (2S,3E)-5-[(tert-butyldiphenylsilanyl)oxy]-1-(3,3-dimethyloxiran-2-yl)-3-methylpent-3-en-2-yl acetate

There total 3 articles about (2S,3E)-5-[(tert-butyldiphenylsilanyl)oxy]-1-(3,3-dimethyloxiran-2-yl)-3-methylpent-3-en-2-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: 82.0%

: 1068574-67-3
(2E,4S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethylocta-2,6-dien-4-yl acetate

: 1285628-22-9
(2S,3E)-5-[(tert-butyldiphenylsilanyl)oxy]-1-(3,3-dimethyloxiran-2-yl)-3-methylpent-3-en-2-yl acetate

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; at 0 ℃; for 3h;
DOI:10.1002/ejoc.201001315

Reference yield:

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

: 1285628-22-9
(2S,3E)-5-[(tert-butyldiphenylsilanyl)oxy]-1-(3,3-dimethyloxiran-2-yl)-3-methylpent-3-en-2-yl acetate

Guidance literature:: Multi-step reaction with 3 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

With dmap; 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:

: (Δ^2,3E)-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1,4-diol

: 1285628-22-9
(2S,3E)-5-[(tert-butyldiphenylsilanyl)oxy]-1-(3,3-dimethyloxiran-2-yl)-3-methylpent-3-en-2-yl acetate

Guidance literature:: Multi-step reaction with 4 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 15 h / 20 °C

2: (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

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

4: 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 3 h / 0 °C

With dmap; 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; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene;
DOI:10.1002/ejoc.201001315