(R)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl 4-methylbenzenesulfonate

Base Information

Chemical Name:(R)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl 4-methylbenzenesulfonate
CAS No.:1443526-62-2
Molecular Formula:C₂₅H₂₄O₆S
Molecular Weight:452.528
Hs Code.:

Synonyms:(R)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl 4-methylbenzenesulfonate

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Chemical Property of (R)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl 4-methylbenzenesulfonate

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Technology Process of (R)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl 4-methylbenzenesulfonate

There total 9 articles about (R)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl 4-methylbenzenesulfonate 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:

: 1443526-61-1
(E)-3’,5’-dihydroxy-3-methoxy-2-(4-((methoxycarbonyl)oxy)-3-methylbut-2-en-1-yl)-[1,1'-biphenyl]-4-yl 4-methylbenzenesulfonate

: (S)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl-4-methylbenzenesulfonate

: 1443526-62-2
(R)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl 4-methylbenzenesulfonate

Guidance literature:: With potassium acetate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; at 40 ℃; for 12h; Reagent/catalyst; Solvent; Concentration; Overall yield = 94 %; Overall yield = 99 mg; enantioselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2013.05.007

Reference yield:

: C₁₅H₂₃BrO₃Si

: (S)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl-4-methylbenzenesulfonate

: 1443526-62-2
(R)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 8 steps

1: hydrogenchloride / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere; Reflux

2: dichloromethane / 1 h / 20 °C / Inert atmosphere

3: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; toluene / 24 h / 90 °C / Inert atmosphere

5: diisobutylaluminium hydride / dichloromethane; hexane / 3 h / -78 - 20 °C / Inert atmosphere

6: dmap; pyridine / chloroform / 3 h / 0 - 20 °C / Inert atmosphere

7: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

8: bis(dibenzylideneacetone)-palladium⁽⁰⁾; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; potassium acetate / methanol; tetrahydrofuran / 12 h / 40 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; tetrabutyl ammonium fluoride; potassium acetate; diisobutylaluminium hydride; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; toluene; 4: |Suzuki-Miyaura Coupling / 8: |Friedel-Crafts Alkylation;
DOI:10.1016/j.tet.2013.05.007

Reference yield:

: C₃₇H₅₄O₇SSi₂

: (S)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl-4-methylbenzenesulfonate

: 1443526-62-2
(R)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1: dmap; pyridine / chloroform / 3 h / 0 - 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

3: bis(dibenzylideneacetone)-palladium⁽⁰⁾; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; potassium acetate / methanol; tetrahydrofuran / 12 h / 40 °C / Inert atmosphere

With pyridine; dmap; tetrabutyl ammonium fluoride; potassium acetate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; chloroform; 3: |Friedel-Crafts Alkylation;
DOI:10.1016/j.tet.2013.05.007