(6E,8E)-(3R,4S,5R)-5-Hydroxy-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester

Base Information

• Chemical Name: (6E,8E)-(3R,4S,5R)-5-Hydroxy-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester
• CAS No.: 1026867-78-6
• Molecular Formula: C₂₆H₃₈O₃Se
• Molecular Weight: 477.546
• Mol file: 1026867-78-6.mol

Synonyms:(6E,8E)-(3R,4S,5R)-5-Hydroxy-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester

Chemical Property of (6E,8E)-(3R,4S,5R)-5-Hydroxy-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6E,8E)-(3R,4S,5R)-5-Hydroxy-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester

There total 23 articles about (6E,8E)-(3R,4S,5R)-5-Hydroxy-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl 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:

4,4-dimethyl-2-pentyne (999-78-0) → (6E,8E)-(3R,4S,5R)-5-Hydroxy-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester (1026867-78-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrahydrofuran / 1.5 h / Heating

2.1: 43 mg / NaOH; H₂O; Pd(PPh₃)4 / tetrahydrofuran / 2 h / Heating

3.1: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; MS₄A / acetonitrile / 0.42 h / 0 - 20 °C

4.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / -78 °C

4.2: 449 mg / tetrahydrofuran; toluene / 0.67 h / -78 - -10 °C

5.1: 66 percent / TFA / CH₂Cl₂ / 22.5 h / -10 - 20 °C

6.1: 138 mg / HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.1: LiOH; H₂O / tetrahydrofuran / 1.5 h / 0 °C

8.1: KHCO₃ / dimethylformamide / 3 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; 18-crown-6 ether; water; potassium hexamethylsilazane; potassium hydrogencarbonate; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Addition / 2.1: Substitution / 3.1: Oxidation / 4.1: deprotonation, Still-Horner olefination / 4.2: Condensation / 5.1: ether cleavage, lactonization / 6.1: Addition / 7.1: Hydrolysis / 8.1: Esterification;

DOI:10.1016/S0040-4020(00)00081-8

Reference yield:

C7H15BO2 → (6E,8E)-(3R,4S,5R)-5-Hydroxy-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester (1026867-78-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 1.178 g / Cs₂CO₃; AsPh₃ / PdCl₂(dppf)2*CH₂Cl₂ / tetrahydrofuran / 24 h / 20 °C

2.1: chemical manganese dioxide / CH₂Cl₂ / 4 h / 20 °C

3.1: dibutylboryl triflate; Et₃N / CH₂Cl₂ / 0 - 3 °C

3.2: 1.429 g / CH₂Cl₂ / 1 h / -78 - -5 °C

4.1: H₂O₂; LiOH / tetrahydrofuran; H₂O / 0.42 h

5.1: 542 mg / KHCO₃ / dimethylformamide / 18 h / 20 °C

6.1: Et₃N; DMAP / CH₂Cl₂ / 2.75 h / 0 - 20 °C

7.1: 712 mg / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 - 0 °C

8.1: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; MS₄A / acetonitrile / 0.42 h / 0 - 20 °C

9.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / -78 °C

9.2: 449 mg / tetrahydrofuran; toluene / 0.67 h / -78 - -10 °C

10.1: 66 percent / TFA / CH₂Cl₂ / 22.5 h / -10 - 20 °C

11.1: 138 mg / HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

12.1: LiOH; H₂O / tetrahydrofuran / 1.5 h / 0 °C

13.1: KHCO₃ / dimethylformamide / 3 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; manganese(IV) oxide; lithium hydroxide; tetrapropylammonium perruthennate; 18-crown-6 ether; triphenyl-arsane; di-n-butylboryl trifluoromethanesulfonate; water; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; caesium carbonate; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Substitution / 2.1: Oxidation / 3.1: enolisation, boration / 3.2: Addition / 4.1: Substitution / 5.1: Esterification / 6.1: Substitution / 7.1: Reduction / 8.1: Oxidation / 9.1: deprotonation, Still-Horner olefination / 9.2: Condensation / 10.1: ether cleavage, lactonization / 11.1: Addition / 12.1: Hydrolysis / 13.1: Esterification;

DOI:10.1016/S0040-4020(00)00081-8

Reference yield:

lithio-phenylselenyl-methane (22859-62-7) → (6E,8E)-(3R,4S,5R)-5-Hydroxy-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester (1026867-78-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 138 mg / HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

2: LiOH; H₂O / tetrahydrofuran / 1.5 h / 0 °C

3: KHCO₃ / dimethylformamide / 3 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; water; potassium hydrogencarbonate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1: Addition / 2: Hydrolysis / 3: Esterification;

DOI:10.1016/S0040-4020(00)00081-8

upstream raw materials:

(2E)-2,4,4-trimethylpent-2-en-1-ol

4,4-dimethyl-2-pentyne

(2E)-2,4,4-trimethylpent-2-enal

lithio-phenylselenyl-methane

Downstream raw materials:

(6E,8E)-(3R,4S,5R)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester