2-Pentanone, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (3S)-

Base Information

• Chemical Name: 2-Pentanone, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (3S)-
• CAS No.: 188899-12-9
• Molecular Formula: C17H38O3Si2
• Molecular Weight: 346.658

Synonyms:

Chemical Property of 2-Pentanone, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Pentanone, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (3S)-

There total 1 articles about 2-Pentanone, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (3S)- 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: 80.0%

(S)-2,2,3,3,9,9,10,10-octamethyl-5-vinyl-4,8-dioxa-3,9-disilaundecane → (-)-(3S)-3,5-bis(tert-butyldimethylsilyloxy)-pentan-2-one (188899-12-9) + (3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxypentan-2-one (218615-21-5)

Guidance literature:

With oxygen; copper diacetate; palladium dichloride; at 40 ℃; for 24h;

DOI:10.1055/s-0036-1591942

Reference yield:

(-)-(3S)-3,5-bis(tert-butyldimethylsilyloxy)-pentan-2-one (188899-12-9) → epothilone D (189453-10-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere

1.2: 14 h / -75 - 30 °C

2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere

4.2: 0.75 h / -75 - -35 °C / Inert atmosphere

5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere

5.2: 2 h / 25 - 30 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere

7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere

7.2: 1 h / -78 °C

8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere

9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C

10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere

11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere

13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere

13.2: 3 h / 0 - 30 °C / Inert atmosphere

14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere

With 2,6-dimethylpyridine; sodium chlorite; n-butyllithium; sodium dihydrogenphosphate dihydrate; 2,4,6-trichlorobenzoyl chloride; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; toluene; tert-butyl alcohol;

Reference yield:

(-)-(3S)-3,5-bis(tert-butyldimethylsilyloxy)-pentan-2-one (188899-12-9) → ixabepilone (219989-84-1)

Guidance literature:

Multi-step reaction with 18 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere

1.2: 14 h / -75 - 30 °C

2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere

4.2: 0.75 h / -75 - -35 °C / Inert atmosphere

5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere

5.2: 2 h / 25 - 30 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere

7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere

7.2: 1 h / -78 °C

8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere

9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C

10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere

11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere

13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere

13.2: 3 h / 0 - 30 °C / Inert atmosphere

14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere

15.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere

16.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere

17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere

18.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere

With 2,6-dimethylpyridine; sodium chlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium azide; sodium dihydrogenphosphate dihydrate; 2,4,6-trichlorobenzoyl chloride; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; trimethylphosphane; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

Downstream raw materials:

(3S,4R,5E)-3-[(tert-butyldimethylsilyl)oxy]-4-methyl-6-phenyl-5-hexenal

(3S,4R,5E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-6-phenylhex-5-en-1-ol

{(1E,3R,4S)-4,6-bis{[(tert-butyl)dimethylsilyl]oxy}-3-methylhex-1-enyl}benzene

5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-1-phenyl-1H-tetrazole

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