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

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Chemical Name:(3S,4R)-(+)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-3-(2Z-octenyl)cyclopent-1-ene
CAS No.:865302-31-4
Molecular Formula:C₃₅H₅₃BrO₂Si₂
Molecular Weight:641.88
Hs Code.:

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

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

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

There total 10 articles about (3S,4R)-(+)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-3-(2Z-octenyl)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: 70.0%

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

: 4762-26-9
hexyltriphenylphosphonium bromide

: 865302-31-4
(3S,4R)-(+)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-3-(2Z-octenyl)cyclopent-1-ene

Guidance literature:: hexyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - -30 ℃;

(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-ene-acetaldehyde; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1021/ol051415y

Reference yield:

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

: 865302-31-4
(3S,4R)-(+)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-3-(2Z-octenyl)cyclopent-1-ene

Guidance literature:: Multi-step reaction with 6 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

6.1: NaHMDS / tetrahydrofuran / -78 - -30 °C

6.2: 70 percent / tetrahydrofuran / 1 h / -78 °C

With pyridine; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; bromine; sodium acetate; sodium hexamethyldisilazane; silica gel; Dess-Martin periodane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetonitrile; benzene; 6.2: Wittig reaction;
DOI:10.1021/ol051415y

Reference yield:

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

: 865302-31-4
(3S,4R)-(+)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-3-(2Z-octenyl)cyclopent-1-ene

Guidance literature:: Multi-step reaction with 7 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

7.1: NaHMDS / tetrahydrofuran / -78 - -30 °C

7.2: 70 percent / tetrahydrofuran / 1 h / -78 °C

With pyridine; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; bromine; sodium acetate; sodium hexamethyldisilazane; silica gel; diisobutylaluminium hydride; Dess-Martin periodane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; cyclohexane; acetonitrile; benzene; 7.2: Wittig reaction;
DOI:10.1021/ol051415y