(3aR,8S,8aR,9R,9aR)-2,2-dimethyl-8-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-9-(triiso-propylsilyloxy)-octahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-one

Base Information

Chemical Name:(3aR,8S,8aR,9R,9aR)-2,2-dimethyl-8-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-9-(triiso-propylsilyloxy)-octahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-one
CAS No.:914616-16-3
Molecular Formula:C₃₇H₆₅NO₄Si
Molecular Weight:616.013
Hs Code.:

Synonyms:(3aR,8S,8aR,9R,9aR)-2,2-dimethyl-8-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-9-(triiso-propylsilyloxy)-octahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-one

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Chemical Property of (3aR,8S,8aR,9R,9aR)-2,2-dimethyl-8-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-9-(triiso-propylsilyloxy)-octahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-one

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Technology Process of (3aR,8S,8aR,9R,9aR)-2,2-dimethyl-8-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-9-(triiso-propylsilyloxy)-octahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-one

There total 7 articles about (3aR,8S,8aR,9R,9aR)-2,2-dimethyl-8-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-9-(triiso-propylsilyloxy)-octahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-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: 90.0%

: 914616-15-2
(3aR,8S,8aR,9R,9aR)-2,2-dimethyl-8-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-9-(triiso-propylsilyloxy)-hexahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-one

: 914616-16-3
(3aR,8S,8aR,9R,9aR)-2,2-dimethyl-8-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-9-(triiso-propylsilyloxy)-octahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-one

Guidance literature:: (3aR,8S,8aR,9R,9aR)-2,2-dimethyl-8-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-9-(triiso-propylsilyloxy)-hexahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-one; With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h;

With sodium hydroxide; water; at 20 ℃;
DOI:10.1021/ol0617751

Reference yield:

: 5-(1-hydroxyallyl)-4-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)pyrrolidin-2-one

: 914616-16-3
(3aR,8S,8aR,9R,9aR)-2,2-dimethyl-8-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-9-(triiso-propylsilyloxy)-octahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: i-Pr₂NEt / CH₂Cl₂

1.2: 81 percent / AcOH / tetrahydrofuran; H₂O

2.1: n-Bu₄N; H₂SO₄ / CH₂Cl₂; aq. NaOH / 20 °C

3.1: Grubbs II catalyst / CH₂Cl₂ / Heating

4.1: Me₃NO; OsO₄ / 2-methyl-propan-2-ol; CH₂Cl₂; H₂O / 24 h / 20 °C

5.1: 169 mg / PTSA / toluene / 3 h

6.1: LiAlH₄ / tetrahydrofuran / 2 h

6.2: 90 percent / aq.NaOH; water / 20 °C

With osmium(VIII) oxide; lithium aluminium tetrahydride; trimethylamine-N-oxide; teterabutylammonium; sulfuric acid; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid; In tetrahydrofuran; sodium hydroxide; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1021/ol0617751

Reference yield:

: 914616-21-0
(1S,8S,8aR)-1-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-8-(triisopropylsilyloxy)-8,8a-dihydroindolizin-3(1H,2H,5H)-one

: 914616-16-3
(3aR,8S,8aR,9R,9aR)-2,2-dimethyl-8-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-9-(triiso-propylsilyloxy)-octahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: Me₃NO; OsO₄ / 2-methyl-propan-2-ol; CH₂Cl₂; H₂O / 24 h / 20 °C

2.1: 169 mg / PTSA / toluene / 3 h

3.1: LiAlH₄ / tetrahydrofuran / 2 h

3.2: 90 percent / aq.NaOH; water / 20 °C

With osmium(VIII) oxide; lithium aluminium tetrahydride; trimethylamine-N-oxide; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1021/ol0617751