(2Z,6Z)-6-Cyclopropyl-10-methylene-2-(3-phenylselanylcarbonyl-propyl)-undeca-2,6-dienedioic acid dimethyl ester

Base Information

• Chemical Name: (2Z,6Z)-6-Cyclopropyl-10-methylene-2-(3-phenylselanylcarbonyl-propyl)-undeca-2,6-dienedioic acid dimethyl ester
• CAS No.: 204325-24-6
• Molecular Formula: C₂₇H₃₄O₅Se
• Molecular Weight: 517.524
• Mol file: 204325-24-6.mol

Synonyms:

Chemical Property of (2Z,6Z)-6-Cyclopropyl-10-methylene-2-(3-phenylselanylcarbonyl-propyl)-undeca-2,6-dienedioic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,6Z)-6-Cyclopropyl-10-methylene-2-(3-phenylselanylcarbonyl-propyl)-undeca-2,6-dienedioic acid dimethyl ester

There total 10 articles about (2Z,6Z)-6-Cyclopropyl-10-methylene-2-(3-phenylselanylcarbonyl-propyl)-undeca-2,6-dienedioic acid dimethyl ester 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:

dicyclopropyl ketone (1121-37-5) → (2Z,6Z)-6-Cyclopropyl-10-methylene-2-(3-phenylselanylcarbonyl-propyl)-undeca-2,6-dienedioic acid dimethyl ester (204325-24-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) MeMgBr, Mg / 1.) THF, -30 deg C; 70 deg C

2: 97 percent / imidazole

3: 64 percent / NIS, PPh₃ / CH₂Cl₂ / -30 °C

4: 73 percent / NaH / dimethylsulfoxide

5: 85 percent / NaH

6: TBAF

7: 87 percent / NaH / 0 °C

8: TBAF

9: Dess-Martin periodinane

10: 1.) KH₂PO₄, aq. NaClO₂, 2-methylbut-2-ene, 2.) PBu₃ / 1.) t-BuOH, 2.) -30 deg C

With 1H-imidazole; sodium chlorite; potassium dihydrogenphosphate; N-iodo-succinimide; 2-methyl-but-2-ene; tributylphosphine; methylmagnesium bromide; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; magnesium; triphenylphosphine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1039/a707320h

Reference yield:

1,1-Dicyclopropyl-butane-1,4-diol (204325-20-2) → (2Z,6Z)-6-Cyclopropyl-10-methylene-2-(3-phenylselanylcarbonyl-propyl)-undeca-2,6-dienedioic acid dimethyl ester (204325-24-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / imidazole

2: 64 percent / NIS, PPh₃ / CH₂Cl₂ / -30 °C

3: 73 percent / NaH / dimethylsulfoxide

4: 85 percent / NaH

5: TBAF

6: 87 percent / NaH / 0 °C

7: TBAF

8: Dess-Martin periodinane

9: 1.) KH₂PO₄, aq. NaClO₂, 2-methylbut-2-ene, 2.) PBu₃ / 1.) t-BuOH, 2.) -30 deg C

With 1H-imidazole; sodium chlorite; potassium dihydrogenphosphate; N-iodo-succinimide; 2-methyl-but-2-ene; tributylphosphine; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; triphenylphosphine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1039/a707320h

Reference yield:

4-(tert-Butyl-diphenyl-silanyloxy)-1,1-dicyclopropyl-butan-1-ol (204325-28-0) → (2Z,6Z)-6-Cyclopropyl-10-methylene-2-(3-phenylselanylcarbonyl-propyl)-undeca-2,6-dienedioic acid dimethyl ester (204325-24-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 64 percent / NIS, PPh₃ / CH₂Cl₂ / -30 °C

2: 73 percent / NaH / dimethylsulfoxide

3: 85 percent / NaH

4: TBAF

5: 87 percent / NaH / 0 °C

6: TBAF

7: Dess-Martin periodinane

8: 1.) KH₂PO₄, aq. NaClO₂, 2-methylbut-2-ene, 2.) PBu₃ / 1.) t-BuOH, 2.) -30 deg C

With sodium chlorite; potassium dihydrogenphosphate; N-iodo-succinimide; 2-methyl-but-2-ene; tributylphosphine; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; triphenylphosphine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1039/a707320h

upstream raw materials:

N-phenylselanylphthalimide

(2Z,6Z)-6-Cyclopropyl-10-methylene-2-(4-oxo-butyl)-undeca-2,6-dienedioic acid dimethyl ester

dicyclopropyl ketone

1,1-Dicyclopropyl-butane-1,4-diol