(S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-hex-5-en-2-ol

Base Information

• Chemical Name: (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-hex-5-en-2-ol
• CAS No.: 90461-03-3
• Molecular Formula: C₂₉H₄₂O₃Si
• Molecular Weight: 466.736

Synonyms:

Chemical Property of (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-hex-5-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-hex-5-en-2-ol

There total 15 articles about (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-hex-5-en-2-ol 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: 91.0%

allylmagnesium bromide (2622-05-1) + tert-Butyl-{(R)-1-[(2S,5R)-2-methyl-5-((S)-2-methyl-oxiranyl)-tetrahydro-furan-2-yl]-ethoxy}-diphenyl-silane (90461-02-2) → (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-hex-5-en-2-ol (90461-03-3)

Guidance literature:

In tetrahydrofuran; for 36h; Ambient temperature;

DOI:10.1021/jo00188a014

Reference yield:

Acetic acid (1E,3Z,5E)-7-hydroxy-2,6-dimethyl-hepta-1,3,5-trienyl ester → (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-hex-5-en-2-ol (90461-03-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 50 percent / 1.) Ti(O-i-Pr)4, (-)-Diethyl D-tartrate, t-BuOOH, / CH₂Cl₂ / -15 °C

2: 94.7 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

3: 94 percent / 5percent HClO₄ / acetonitrile / 4 h / Ambient temperature

4: 90 percent / Phosphorus oxychloride / CH₂Cl₂ / 24 h / Ambient temperature

5: 90 percent / K₂CO₃ / methanol / 1 h / 0 °C

6: 83 percent / Dowex H⁺ / methanol / 24 h / Ambient temperature

7: 60 percent / 1.) Ti(O-i-Pr), (-)-Diethyl D-tatrate, t-BuOOH, 2.) Tattratic acid / CH₂Cl₂ / 1.) -23 degC, 30 min. 2.) stirring

8: 82.5 percent / pyridine / 0 °C / overnight

9: NaI / butan-2-one / 3 h / Heating

10: 98.4 percent / Tri-n-butyltin hydride / ethanol / 2 h / Ambient temperature

11: Imidazole / dimethylformamide / 3 h / 60 °C

12: 95.3 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

13: pyridine / 0 °C

14: K₂CO₃ / methanol / 1 h / Ambient temperature

15: 91 percent / tetrahydrofuran / 36 h / Ambient temperature

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; perchloric acid; diethyl (2S,3S)-tartrate; Dowex H⁺; Tattratic acid; tri-n-butyl-tin hydride; potassium carbonate; (-)-diethyl tartrate; triethylamine; sodium iodide; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; butanone;

DOI:10.1021/jo00188a014

Reference yield:

(S)-4-((E)-(R)-1,6-Dihydroxy-4-methyl-hex-4-enyl)-4-methyl-[1,3]dioxolan-2-one (90460-97-2) → (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-hex-5-en-2-ol (90461-03-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 60 percent / 1.) Ti(O-i-Pr), (-)-Diethyl D-tatrate, t-BuOOH, 2.) Tattratic acid / CH₂Cl₂ / 1.) -23 degC, 30 min. 2.) stirring

2: 82.5 percent / pyridine / 0 °C / overnight

3: NaI / butan-2-one / 3 h / Heating

4: 98.4 percent / Tri-n-butyltin hydride / ethanol / 2 h / Ambient temperature

5: Imidazole / dimethylformamide / 3 h / 60 °C

6: 95.3 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

7: pyridine / 0 °C

8: K₂CO₃ / methanol / 1 h / Ambient temperature

9: 91 percent / tetrahydrofuran / 36 h / Ambient temperature

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; Tattratic acid; tri-n-butyl-tin hydride; potassium carbonate; (-)-diethyl tartrate; sodium iodide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; butanone;

DOI:10.1021/jo00188a014

upstream raw materials:

allylmagnesium bromide

tert-Butyl-{(R)-1-[(2S,5R)-2-methyl-5-((S)-2-methyl-oxiranyl)-tetrahydro-furan-2-yl]-ethoxy}-diphenyl-silane

(E)-5-((2R,3R)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl acetate

(S)-4-((E)-(R)-1,6-Dihydroxy-4-methyl-hex-4-enyl)-4-methyl-[1,3]dioxolan-2-one

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 90461-03-3 (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-hex-5-en-2-ol

Send

Send

Metric Ton KG G Pound L ML

Send

Send