(3S,4R)-(+)-2-bromo-3-ethenyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-1-ene

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Chemical Name:(3S,4R)-(+)-2-bromo-3-ethenyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-1-ene
CAS No.:865302-29-0
Molecular Formula:C₂₉H₄₁BrO₂Si₂
Molecular Weight:557.718
Hs Code.:

Synonyms:(3S,4R)-(+)-2-bromo-3-ethenyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-1-ene

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Chemical Property of (3S,4R)-(+)-2-bromo-3-ethenyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-1-ene

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Technology Process of (3S,4R)-(+)-2-bromo-3-ethenyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-1-ene

There total 7 articles about (3S,4R)-(+)-2-bromo-3-ethenyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-1-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: 84.0%

: 1826-67-1
vinyl magnesium bromide

: 122552-67-4
(4R)-(+)-2-bromo-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-en-1-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 865302-29-0
(3S,4R)-(+)-2-bromo-3-ethenyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-1-ene

Guidance literature:: vinyl magnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -20 ℃; for 0.333333h;

(4R)-(+)-2-bromo-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-en-1-one; In tetrahydrofuran; at -78 ℃; for 0.25h;

tert-butyldimethylsilyl chloride; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -20 - 0 ℃;
DOI:10.1021/ol051415y

Reference yield:

: 817210-68-7
(1S,4R)-(+)-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-en-1-ol

: 865302-29-0
(3S,4R)-(+)-2-bromo-3-ethenyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-1-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 96 percent / sodium acetate; silica gel; pyridinium chlorochromate / CH₂Cl₂ / 2 h / 22 °C

2.1: bromine / CH₂Cl₂ / 1 h / 0 °C

2.2: 96 percent / triethylamine / CH₂Cl₂ / 1 h / 22 °C

3.1: copper(I) iodide / tetrahydrofuran / 0.33 h / -20 °C

3.2: tetrahydrofuran / 0.25 h / -78 °C

3.3: 84 percent / HMPA / tetrahydrofuran / -20 - 0 °C

With copper(l) iodide; bromine; sodium acetate; silica gel; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol051415y

Reference yield:

: 865302-28-9
(3R,5S)-(+)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(trimethylacetyloxy)cyclopent-1-ene

: 865302-29-0
(3S,4R)-(+)-2-bromo-3-ethenyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-1-ene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / DIBAL / cyclohexane; CH₂Cl₂ / 0.5 h / -78 °C

2.1: 96 percent / sodium acetate; silica gel; pyridinium chlorochromate / CH₂Cl₂ / 2 h / 22 °C

3.1: bromine / CH₂Cl₂ / 1 h / 0 °C

3.2: 96 percent / triethylamine / CH₂Cl₂ / 1 h / 22 °C

4.1: copper(I) iodide / tetrahydrofuran / 0.33 h / -20 °C

4.2: tetrahydrofuran / 0.25 h / -78 °C

4.3: 84 percent / HMPA / tetrahydrofuran / -20 - 0 °C

With copper(l) iodide; bromine; sodium acetate; silica gel; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; cyclohexane;
DOI:10.1021/ol051415y