(+)-11,15-dibenzylidene-(14S)-(tert-butyldimethylsilanyloxy)-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxaicyclo[15.2.1]icosane-7-one

Base Information

Chemical Name:(+)-11,15-dibenzylidene-(14S)-(tert-butyldimethylsilanyloxy)-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxaicyclo[15.2.1]icosane-7-one
CAS No.:662168-64-1
Molecular Formula:C₄₄H₆₆O₄Si
Molecular Weight:687.091
Hs Code.:

Synonyms:(+)-11,15-dibenzylidene-(14S)-(tert-butyldimethylsilanyloxy)-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxaicyclo[15.2.1]icosane-7-one

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Chemical Property of (+)-11,15-dibenzylidene-(14S)-(tert-butyldimethylsilanyloxy)-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxaicyclo[15.2.1]icosane-7-one

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Technology Process of (+)-11,15-dibenzylidene-(14S)-(tert-butyldimethylsilanyloxy)-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxaicyclo[15.2.1]icosane-7-one

There total 15 articles about (+)-11,15-dibenzylidene-(14S)-(tert-butyldimethylsilanyloxy)-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxaicyclo[15.2.1]icosane-7-one 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: 84.0%

: 662168-56-1
(-)-11,15-dibenzylidene-(14S)-hydroxy-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxabicyclo[15.2.1]icosan-7-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 662168-64-1
(+)-11,15-dibenzylidene-(14S)-(tert-butyldimethylsilanyloxy)-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxaicyclo[15.2.1]icosane-7-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1021/ja042733f

Reference yield:

: 850341-32-1
(-)-4-[(3S)-methyl-(5R)-(prop-2-ynyl)tetrahydrofuran-(2S)-yl]butan-1-ol

: 662168-64-1
(+)-11,15-dibenzylidene-(14S)-(tert-butyldimethylsilanyloxy)-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxaicyclo[15.2.1]icosane-7-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: Pd(PPh₃)4; CuI; pyrrolidine / 3.5 h / 23 °C

2.1: 73 percent / imidazole; PPh₃; iodine / acetonitrile; diethyl ether / 3.5 h / 0 °C

3.1: LiCl; LDA / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C

3.2: tetrahydrofuran; hexane / 5 h / 0 °C

4.1: 298 mg / aq. NaOH / 2-methyl-propan-2-ol; methanol / 48 h / Heating

5.1: 72 percent / dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / CH₂Cl₂ / 24 h / 23 °C

6.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h

7.1: 84 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.25 h / 23 °C

8.1: Ni(cod)2; PBu₃; Et₃B / toluene / 14 h / 60 °C

9.1: 84 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

With pyrrolidine; 1H-imidazole; 2,6-dimethylpyridine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethyl borane; tributylphosphine; tetrabutyl ammonium fluoride; iodine; Dess-Martin periodane; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 1.1: Sonogashira coupling;
DOI:10.1021/ja042733f

Reference yield:

: (S)-2-Methyl-6-[(2S,3S)-3-methyl-5-(3-phenyl-prop-2-ynyl)-tetrahydro-furan-2-yl]-hexanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

: 662168-64-1
(+)-11,15-dibenzylidene-(14S)-(tert-butyldimethylsilanyloxy)-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxaicyclo[15.2.1]icosane-7-one

Guidance literature:: Multi-step reaction with 6 steps

1: 298 mg / aq. NaOH / 2-methyl-propan-2-ol; methanol / 48 h / Heating

2: 72 percent / dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / CH₂Cl₂ / 24 h / 23 °C

3: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h

4: 84 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.25 h / 23 °C

5: Ni(cod)2; PBu₃; Et₃B / toluene / 14 h / 60 °C

6: 84 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

With 2,6-dimethylpyridine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sodium hydroxide; triethyl borane; tributylphosphine; tetrabutyl ammonium fluoride; Dess-Martin periodane; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/ja042733f