<2(R),4(Z),S(R)> 2-t-butyldimethylsilyloxy 1-p-tolylsulfinyl 4-decene

Base Information

• Chemical Name: <2(R),4(Z),S(R)> 2-t-butyldimethylsilyloxy 1-p-tolylsulfinyl 4-decene
• CAS No.: 136580-81-9
• Molecular Formula: C₂₃H₄₀O₂SSi
• Molecular Weight: 408.721
• Mol file: 136580-81-9.mol

Synonyms:<2(R),4(Z),S(R)> 2-t-butyldimethylsilyloxy 1-p-tolylsulfinyl 4-decene

Chemical Property of <2(R),4(Z),S(R)> 2-t-butyldimethylsilyloxy 1-p-tolylsulfinyl 4-decene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2(R),4(Z),S(R)> 2-t-butyldimethylsilyloxy 1-p-tolylsulfinyl 4-decene

There total 6 articles about <2(R),4(Z),S(R)> 2-t-butyldimethylsilyloxy 1-p-tolylsulfinyl 4-decene 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: 89.0%

<2(R),4(Z),S(R)> 1-p-tolylsulfinyl 4-decen-2-ol (121824-08-6) + tert-butyldimethylsilyl chloride (18162-48-6) → <2(R),4(Z),S(R)> 2-t-butyldimethylsilyloxy 1-p-tolylsulfinyl 4-decene (136580-81-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 14h;

DOI:10.1016/S0957-4166(00)82171-0

Reference yield:

(Z)-1-iodohept-1-ene (63318-29-6) → <2(R),4(Z),S(R)> 2-t-butyldimethylsilyloxy 1-p-tolylsulfinyl 4-decene (136580-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) a) BuLi, b) CuCN / 1.) ether, hexane, a) -78 deg C, 45 min, b) -25 deg C, 30 min, 2.) ether, hexane, -60 deg C, 40 min

2: 89 percent / imidazole / dimethylformamide / 14 h / 25 °C

With 1H-imidazole; n-butyllithium; In N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(00)82171-0

Reference yield:

(R)-methyl p-tolyl sulfoxide (1519-39-7) → <2(R),4(Z),S(R)> 2-t-butyldimethylsilyloxy 1-p-tolylsulfinyl 4-decene (136580-81-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) LDA / 1.) THF, hexane, -40 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

2: ZnCl₂, DIBAL / tetrahydrofuran; toluene / 0.5 h / -78 °C

3: 85 percent / 20percent aq. K₂CO₃ / acetonitrile / 9 h / Ambient temperature

4: 1.) a) BuLi, b) CuCN / 1.) ether, hexane, a) -78 deg C, 45 min, b) -25 deg C, 30 min, 2.) ether, hexane, -60 deg C, 40 min

5: 89 percent / imidazole / dimethylformamide / 14 h / 25 °C

With 1H-imidazole; n-butyllithium; diisobutylaluminium hydride; potassium carbonate; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0957-4166(00)82171-0

upstream raw materials:

<2(R),4(Z),S(R)> 1-p-tolylsulfinyl 4-decen-2-ol

tert-butyldimethylsilyl chloride

(Z)-1-iodohept-1-ene

(R)-methyl p-tolyl sulfoxide

Downstream raw materials:

Acetic acid (Z)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-p-tolylsulfanyl-dec-4-enyl ester