(1E,4S,5R)-5-tert-butyldiphenylsilyloxy-1-iodo-4-methyl-hex-1-ene

Base Information

• Chemical Name: (1E,4S,5R)-5-tert-butyldiphenylsilyloxy-1-iodo-4-methyl-hex-1-ene
• CAS No.: 945903-68-4
• Molecular Formula: C₂₃H₃₁IOSi
• Molecular Weight: 478.489
• Mol file: 945903-68-4.mol

Synonyms:(1E,4S,5R)-5-tert-butyldiphenylsilyloxy-1-iodo-4-methyl-hex-1-ene

Chemical Property of (1E,4S,5R)-5-tert-butyldiphenylsilyloxy-1-iodo-4-methyl-hex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1E,4S,5R)-5-tert-butyldiphenylsilyloxy-1-iodo-4-methyl-hex-1-ene

There total 5 articles about (1E,4S,5R)-5-tert-butyldiphenylsilyloxy-1-iodo-4-methyl-hex-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: 78.0%

(3S,4R)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-al (945903-67-3) + iodoform (75-47-8) → (1E,4S,5R)-5-tert-butyldiphenylsilyloxy-1-iodo-4-methyl-hex-1-ene (945903-68-4)

Guidance literature:

With chromium dichloride; In tetrahydrofuran; 1,4-dioxane; at 0 ℃; for 24h;

DOI:10.1016/j.tet.2007.04.061

Reference yield:

(3S,4R)-4-tert-butyldiphenylsilyloxy-3-methyl-pent-1-ene (945903-65-1) → (1E,4S,5R)-5-tert-butyldiphenylsilyloxy-1-iodo-4-methyl-hex-1-ene (945903-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BH₃*SMe₂ / hexane; tetrahydrofuran / 26 h / 20 °C

1.2: 69 percent / aq. NaOH; H₂O₂ / hexane; tetrahydrofuran / 20 °C

2.1: 68 percent / pyridinium dichromate / CH₂Cl₂ / 3 h / 20 °C

3.1: 78 percent / CrCl₂ / tetrahydrofuran; dioxane / 24 h / 0 °C

With chromium dichloride; dipyridinium dichromate; dimethylsulfide borane complex; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane;

DOI:10.1016/j.tet.2007.04.061

Reference yield:

(3S,4R)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-ol (945903-66-2) → (1E,4S,5R)-5-tert-butyldiphenylsilyloxy-1-iodo-4-methyl-hex-1-ene (945903-68-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / pyridinium dichromate / CH₂Cl₂ / 3 h / 20 °C

2: 78 percent / CrCl₂ / tetrahydrofuran; dioxane / 24 h / 0 °C

With chromium dichloride; dipyridinium dichromate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1016/j.tet.2007.04.061

upstream raw materials:

(3S,4R)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-al

iodoform

(3S,4R)-4-tert-butyldiphenylsilyloxy-3-methyl-pent-1-ene

(3S,4R)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-ol

Downstream raw materials:

(1E,3E,6S,7R)-7-tert-butyldiphenylsilyloxy-6-methyl-1-phenylocta-1,3-diene