(3R,4S,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide

Base Information

Chemical Name:(3R,4S,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide
CAS No.:218778-72-4
Molecular Formula:C₂₃H₃₂O₂Se
Molecular Weight:419.466
Hs Code.:

Synonyms:(3R,4S,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide

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Chemical Property of (3R,4S,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide

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Technology Process of (3R,4S,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide

There total 21 articles about (3R,4S,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide 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: 73.0%

: 22859-62-7
lithio-phenylselenyl-methane

: 218778-69-9
(4S,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-2-pentene-5-olide

: 218778-72-4
(3R,4S,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran;
DOI:10.1021/jo981744m

Reference yield:

: 999-78-0
4,4-dimethyl-2-pentyne

: 218778-72-4
(3R,4S,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide

Guidance literature:: Multi-step reaction with 6 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

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; 18-crown-6 ether; water; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; 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;
DOI:10.1016/S0040-4020(00)00081-8

Reference yield:

: C₇H₁₅BO₂

: 218778-72-4
(3R,4S,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide

Guidance literature:: Multi-step reaction with 11 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

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