3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methylene-4-(triethylsilyloxy)cyclopent-2-enone

Base Information

Chemical Name:3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methylene-4-(triethylsilyloxy)cyclopent-2-enone
CAS No.:1384870-55-6
Molecular Formula:C₃₅H₅₀O₅Si₂
Molecular Weight:606.95
Hs Code.:

Synonyms:3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methylene-4-(triethylsilyloxy)cyclopent-2-enone

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Chemical Property of 3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methylene-4-(triethylsilyloxy)cyclopent-2-enone

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Technology Process of 3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methylene-4-(triethylsilyloxy)cyclopent-2-enone

There total 9 articles about 3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methylene-4-(triethylsilyloxy)cyclopent-2-enone 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: 85.0%

: 1384870-79-4
3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-4-(triethylsilyloxy)cyclopent-2-enone

: 33797-51-2
eschenmoser's salt

: 1384870-55-6
3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methylene-4-(triethylsilyloxy)cyclopent-2-enone

Guidance literature:: 3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-4-(triethylsilyloxy)cyclopent-2-enone; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; benzene; at -78 ℃; for 1h;

eschenmoser's salt; In tetrahydrofuran; n-heptane; benzene; at -78 - 20 ℃; for 2.5h;
DOI:10.1021/ol301513h

Reference yield:

: 5554-99-4
(2-methylfuran-3-yl)methanol

: 1384870-55-6
3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methylene-4-(triethylsilyloxy)cyclopent-2-enone

Guidance literature:: Multi-step reaction with 7 steps

1.1: bromine / diethyl ether / 3 h / -78 °C

1.2: 1 h / -78 - 20 °C

2.1: hydroquinone / 3.5 h / pH 6.3 / aq. phosphate buffer; Reflux

3.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

4.1: tert.-butyl lithium / diethyl ether; pentane / 1.75 h / -78 - 20 °C / Inert atmosphere

4.2: 2 h / -78 - 20 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

6.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C / Inert atmosphere

7.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; benzene / 1 h / -78 °C

7.2: 2.5 h / -78 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; bromine; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; hydroquinone; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; N,N-dimethyl-formamide; pentane; benzene;
DOI:10.1021/ol301513h

Reference yield:

: 76374-24-8,76374-33-9,90371-07-6
2,5-dihydro-3-hydroxymethyl-2,5-dimethoxy-2-methylfuran

: 1384870-55-6
3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methylene-4-(triethylsilyloxy)cyclopent-2-enone

Guidance literature:: Multi-step reaction with 6 steps

1.1: hydroquinone / 3.5 h / pH 6.3 / aq. phosphate buffer; Reflux

2.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: tert.-butyl lithium / diethyl ether; pentane / 1.75 h / -78 - 20 °C / Inert atmosphere

3.2: 2 h / -78 - 20 °C / Inert atmosphere

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

5.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C / Inert atmosphere

6.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; benzene / 1 h / -78 °C

6.2: 2.5 h / -78 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; hydroquinone; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; N,N-dimethyl-formamide; pentane; benzene;
DOI:10.1021/ol301513h