(2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran

Base Information

• Chemical Name: (2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran
• CAS No.: 1073828-69-9
• Molecular Formula: C₃₀H₄₁BrO₂Si
• Molecular Weight: 541.644
• Mol file: 1073828-69-9.mol

Synonyms:(2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran

Chemical Property of (2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran

There total 13 articles about (2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran 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%

(2S,5S)-5-[3-(tert-butyldiphenylsilyloxy)propyl]-tetrahydrofuran-2-carboxaldehyde + (R)-5-(4-bromo-2-methyl-4-penten-1-yl)sulfonyl-1-phenyl-1H-tetrazole → (2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran (1073828-69-9)

Guidance literature:

(R)-5-(4-bromo-2-methyl-4-penten-1-yl)sulfonyl-1-phenyl-1H-tetrazole; With potassium hexamethylsilazane; In N,N-dimethyl-formamide; toluene; at -65 ℃; for 0.5h; Inert atmosphere;

(2S,5S)-5-[3-(tert-butyldiphenylsilyloxy)propyl]-tetrahydrofuran-2-carboxaldehyde; In N,N-dimethyl-formamide; toluene; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.joc.7b01973

Reference yield: 78.0%

C6H9BrO (1073828-58-6) + 5-(((2S,5S)-5-(3-(tert-butyldiphenylsilyloxy)propyl)oxolan-2-yl)methylsulfonyl)-1-phenyl-1H-tetrazole (1073828-65-5) → (2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran (1073828-69-9)

Guidance literature:

With potassium hexamethylsilazane; In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; at -78 - 20 ℃; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol801923y

Reference yield:

(2S,5S)-5-[3-(tert-butyldiphenylsilyloxy)propyl]-tetrahydrofuran-2-carboxaldehyde + (R)-5-(4-bromo-2-methyl-4-penten-1-yl)sulfonyl-1-phenyl-1H-tetrazole → (2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran (1073828-69-9) + C30H41BrO2Si

Guidance literature:

(R)-5-(4-bromo-2-methyl-4-penten-1-yl)sulfonyl-1-phenyl-1H-tetrazole; With potassium hexamethylsilazane; In N,N-dimethyl-formamide; at -65 ℃; for 0.5h; Inert atmosphere;

(2S,5S)-5-[3-(tert-butyldiphenylsilyloxy)propyl]-tetrahydrofuran-2-carboxaldehyde; In N,N-dimethyl-formamide; at 20 ℃; for 18h; Reagent/catalyst; Overall yield = 69 %; Inert atmosphere;

DOI:10.1021/acs.joc.7b01973

upstream raw materials:

C₆H₉BrO

5-(((2S,5S)-5-(3-(tert-butyldiphenylsilyloxy)propyl)oxolan-2-yl)methylsulfonyl)-1-phenyl-1H-tetrazole

tert-butyl(pent-4-en-1-yloxy)diphenylsilane

(2S)-5-(tert-butyldiphenylsilyloxy)-1,2-epoxypentane

Downstream raw materials:

(2S,5S)-5-[(1R,2S,3R)-5-bromo-1,2-dihydroxy-3-methyl-5-hexenyl]-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane

(2S,5S)-5-[(1S,2R,3R)-5-bromo-1,2-dihydroxy-3-methyl-5-hexenyl]-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane