1(R)-<(tert-butyldimethylsilyl)oxy>-1-cyclohexyl-3-iodo-2(E)-propene

Base Information

• Chemical Name: 1(R)-<(tert-butyldimethylsilyl)oxy>-1-cyclohexyl-3-iodo-2(E)-propene
• CAS No.: 82476-94-6
• Molecular Formula: C₁₅H₂₉IOSi
• Molecular Weight: 380.385
• Mol file: 82476-94-6.mol

Synonyms:1(R)-<(tert-butyldimethylsilyl)oxy>-1-cyclohexyl-3-iodo-2(E)-propene

Chemical Property of 1(R)-<(tert-butyldimethylsilyl)oxy>-1-cyclohexyl-3-iodo-2(E)-propene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1(R)-<(tert-butyldimethylsilyl)oxy>-1-cyclohexyl-3-iodo-2(E)-propene

There total 3 articles about 1(R)-<(tert-butyldimethylsilyl)oxy>-1-cyclohexyl-3-iodo-2(E)-propene 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: 86.0%

3-cyclohexyl-3R-hydroxy-1-iodoprop-1E-ene (82510-26-7) + tert-butyldimethylsilyl chloride (18162-48-6) → 1(R)-<(tert-butyldimethylsilyl)oxy>-1-cyclohexyl-3-iodo-2(E)-propene (82476-94-6)

Guidance literature:

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

DOI:10.1021/jo00306a007

Reference yield:

3-cyclohexyl-3RS-hydroxy-1-iodoprop-1E-ene (71399-48-9) → 1(R)-<(tert-butyldimethylsilyl)oxy>-1-cyclohexyl-3-iodo-2(E)-propene (82476-94-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / t-BuOOH, L-(+)-DIPT, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH₂Cl₂ / 53 h / -21 °C

2: 86 percent / imidazole / dimethylformamide

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00306a007

Reference yield:

cyclohexanylcarbonyl chloride (2719-27-9) → 1(R)-<(tert-butyldimethylsilyl)oxy>-1-cyclohexyl-3-iodo-2(E)-propene (82476-94-6)

Guidance literature:

Multi-step reaction with 3 steps

2: 42 percent / t-BuOOH, L-(+)-DIPT, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH₂Cl₂ / 53 h / -21 °C

3: 86 percent / imidazole / dimethylformamide

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00306a007

upstream raw materials:

3-cyclohexyl-3R-hydroxy-1-iodoprop-1E-ene

tert-butyldimethylsilyl chloride

3-cyclohexyl-3RS-hydroxy-1-iodoprop-1E-ene

cyclohexanylcarbonyl chloride

Downstream raw materials:

(6Z,8E,10E)-(5S,12R)-5,12-Bis-(tert-butyl-dimethyl-silanyloxy)-12-cyclohexyl-dodeca-6,8,10-trienoic acid

12-cyclohexyl-5(S),12(R)-dodecatrienoic acid

methyl (5Z,12E)-(14R)-14-tert-butyldimethylsilyloxy-14-cyclohexyl-9-oxo-5,12-tetradecadienoate

methyl-(5Z,10E)-(8RS,12R)-8-acetyl-12-tert-butyldimethylsilyloxy-12-cyclohexyl-5,10-dodecadienoate