(4a'S,10a'S)-methyl 4a'-benzyl-9'-hydroxy-3',4',4a',9',10',10a'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate

Base Information

Chemical Name:(4a'S,10a'S)-methyl 4a'-benzyl-9'-hydroxy-3',4',4a',9',10',10a'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate
CAS No.:1400926-95-5
Molecular Formula:C₂₅H₂₈O₅
Molecular Weight:408.494
Hs Code.:

Synonyms:(4a'S,10a'S)-methyl 4a'-benzyl-9'-hydroxy-3',4',4a',9',10',10a'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate

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Chemical Property of (4a'S,10a'S)-methyl 4a'-benzyl-9'-hydroxy-3',4',4a',9',10',10a'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate

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Technology Process of (4a'S,10a'S)-methyl 4a'-benzyl-9'-hydroxy-3',4',4a',9',10',10a'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate

There total 6 articles about (4a'S,10a'S)-methyl 4a'-benzyl-9'-hydroxy-3',4',4a',9',10',10a'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate 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: 92.0%

: 1400926-94-4
(4a'S,10a'S)-methyl 4a'-benzyl-9'-oxo-3',4',4a',9',10',10a'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate

: 1400926-95-5
(4a'S,10a'S)-methyl 4a'-benzyl-9'-hydroxy-3',4',4a',9',10',10a'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate

Guidance literature:: (4a'S,10a'S)-methyl 4a'-benzyl-9'-oxo-3',4',4a',9',10',10a'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate; With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.5h;

With water; In dichloromethane;

Reference yield:

: 1400926-92-2
(S)-4a-benzyl-7-bromo-4,4a,9,10-tetrahydrophenanthren-2(3H)-one

: 1400926-95-5
(4a'S,10a'S)-methyl 4a'-benzyl-9'-hydroxy-3',4',4a',9',10',10a'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: triethylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 15 h / 100 °C / 3102.97 Torr / Inert atmosphere

2: hydrogen / 5%-palladium/activated carbon / pyridine; tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

3: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 4 h / Inert atmosphere

4: pyridine; potassium permanganate; copper(ll) sulfate pentahydrate / dichloromethane; water / 43 h

5: sodium tetrahydroborate / methanol / 0.5 h / 20 °C

With pyridine; sodium tetrahydroborate; potassium permanganate; copper(ll) sulfate pentahydrate; hydrogen; toluene-4-sulfonic acid; triethylamine; trimethyl orthoformate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; 5%-palladium/activated carbon; In tetrahydrofuran; pyridine; methanol; dichloromethane; water;

Reference yield:

: 418772-23-3
(1R,9S,10R)-1-benzyl-5-bromo-10-hydroxy-10-methyl-tricyclo[7.3.1.0(2,7)]trideca-2,4,6-trien-13-one1(R)-benzyl-5-bromo-10(R)-hydroxy-10-methyl-tricyclo[7.3.1.0_2,7]trideca-2,4,6-trien-13-one

: 1400926-95-5
(4a'S,10a'S)-methyl 4a'-benzyl-9'-hydroxy-3',4',4a',9',10',10a'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-phenanthrene]-7'-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: sodium ethanolate / ethanol / 0.5 h / 80 °C / Industry scale

2: triethylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 15 h / 100 °C / 3102.97 Torr / Inert atmosphere

3: hydrogen / 5%-palladium/activated carbon / pyridine; tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

4: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 4 h / Inert atmosphere

5: pyridine; potassium permanganate; copper(ll) sulfate pentahydrate / dichloromethane; water / 43 h

6: sodium tetrahydroborate / methanol / 0.5 h / 20 °C

With pyridine; sodium tetrahydroborate; potassium permanganate; copper(ll) sulfate pentahydrate; hydrogen; sodium ethanolate; toluene-4-sulfonic acid; triethylamine; trimethyl orthoformate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; 5%-palladium/activated carbon; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water;