(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-ene-acetaldehyde

Base Information

Chemical Name:(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-ene-acetaldehyde
CAS No.:865302-30-3
Molecular Formula:C₂₉H₄₁BrO₃Si₂
Molecular Weight:573.718
Hs Code.:

Synonyms:(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-ene-acetaldehyde

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Chemical Property of (1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-ene-acetaldehyde

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Technology Process of (1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-ene-acetaldehyde

There total 9 articles about (1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-ene-acetaldehyde 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:

: (1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-eneethanol

: 865302-30-3
(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-ene-acetaldehyde

Guidance literature:: With pyridine; Dess-Martin periodane; In acetonitrile; benzene; at 22 ℃; for 0.666667h;
DOI:10.1021/ol051415y

Reference yield:

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

: 865302-30-3
(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-ene-acetaldehyde

Guidance literature:: Multi-step reaction with 5 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

4.1: 9-BBN / tetrahydrofuran / -78 - 22 °C

4.2: hydrogen peroxide; NaOH / tetrahydrofuran; H₂O / 0.17 h / -78 °C

5.1: pyridine; Dess-Martin periodinane / benzene; acetonitrile / 0.67 h / 22 °C

With pyridine; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; bromine; sodium acetate; silica gel; Dess-Martin periodane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ol051415y

Reference yield:

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

: 865302-30-3
(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-ene-acetaldehyde

Guidance literature:: Multi-step reaction with 6 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

5.1: 9-BBN / tetrahydrofuran / -78 - 22 °C

5.2: hydrogen peroxide; NaOH / tetrahydrofuran; H₂O / 0.17 h / -78 °C

6.1: pyridine; Dess-Martin periodinane / benzene; acetonitrile / 0.67 h / 22 °C

With pyridine; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; bromine; sodium acetate; silica gel; diisobutylaluminium hydride; Dess-Martin periodane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; cyclohexane; acetonitrile; benzene;
DOI:10.1021/ol051415y