(4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-4,4a,4b,5,8a,9,10,10a-octahydro-1-(2-(triisopropylsilyloxy)ethyl)-8,10-bis(methoxymethoxy)-4a,6-dimethylphenanthren-3(8H)-one

Base Information

Chemical Name:(4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-4,4a,4b,5,8a,9,10,10a-octahydro-1-(2-(triisopropylsilyloxy)ethyl)-8,10-bis(methoxymethoxy)-4a,6-dimethylphenanthren-3(8H)-one
CAS No.:944450-25-3
Molecular Formula:C₄₂H₆₈O₈Si
Molecular Weight:729.083
Hs Code.:

(4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-4,4a,4b,5,8a,9,10,10a-octahydro-1-(2-(triisopropylsilyloxy)ethyl)-8,10-bis(methoxymethoxy)-4a,6-dimethylphenanthren-3(8H)-one

Synonyms:(4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-4,4a,4b,5,8a,9,10,10a-octahydro-1-(2-(triisopropylsilyloxy)ethyl)-8,10-bis(methoxymethoxy)-4a,6-dimethylphenanthren-3(8H)-one

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Chemical Property of (4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-4,4a,4b,5,8a,9,10,10a-octahydro-1-(2-(triisopropylsilyloxy)ethyl)-8,10-bis(methoxymethoxy)-4a,6-dimethylphenanthren-3(8H)-one

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Technology Process of (4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-4,4a,4b,5,8a,9,10,10a-octahydro-1-(2-(triisopropylsilyloxy)ethyl)-8,10-bis(methoxymethoxy)-4a,6-dimethylphenanthren-3(8H)-one

There total 15 articles about (4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-4,4a,4b,5,8a,9,10,10a-octahydro-1-(2-(triisopropylsilyloxy)ethyl)-8,10-bis(methoxymethoxy)-4a,6-dimethylphenanthren-3(8H)-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:

: 944450-14-0
2-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]ethanol

: 944450-25-3
(4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-4,4a,4b,5,8a,9,10,10a-octahydro-1-(2-(triisopropylsilyloxy)ethyl)-8,10-bis(methoxymethoxy)-4a,6-dimethylphenanthren-3(8H)-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 98 percent / sulfur trioxide-pyridine complex; ethyldiisopropylamine; DMSO / CH₂Cl₂ / 0.67 h / -30 - -15 °C

2.1: 78 percent / Zn(OTf)2; (+)-N-methylephedrine; triethylamine / toluene / 15 h / 20 °C

3.1: tributyltin hydride / dichlorobis[tri(o-tolyl)phosphine]palladium / tetrahydrofuran / 0 - 20 °C

3.2: iodine / diethyl ether / 0.25 h / 0 °C

4.1: tributyltin hydride; lithium diisopropylamide; copper cyanide / tetrahydrofuran; diethyl ether; methanol / 0.25 h / -78 - -25 °C

4.2: 1.56 g / copper(I) chloride / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 10 h / 20 °C

5.1: 85 percent / toluene / 28 h / 205 °C

6.1: 92 percent / ethyldiisopropylamine / CH₂Cl₂ / 2 h

7.1: KHMDS / toluene / 0.03 h / -78 °C

7.2: triethylphosphite; oxygen / toluene / 1.25 h / -78 °C

8.1: lithium aluminum hydride / tetrahydrofuran / 1.25 h / 20 °C

8.2: 489 mg / NaIO₄; KH₂PO₄; Na₂HPO₄ / tetrahydrofuran; H₂O / 4.5 h / 0 - 28 °C / pH 7

With lithium aluminium tetrahydride; tri-n-butyl-tin hydride; copper(l) cyanide; sulfur trioxide pyridine complex; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; (+)-N-methylephedrine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1.1: Parikh-Doering oxidation;
DOI:10.1021/jo070165r

Reference yield:

: 944450-15-1
2-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetaldehyde

: 944450-25-3
(4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-4,4a,4b,5,8a,9,10,10a-octahydro-1-(2-(triisopropylsilyloxy)ethyl)-8,10-bis(methoxymethoxy)-4a,6-dimethylphenanthren-3(8H)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 78 percent / Zn(OTf)2; (+)-N-methylephedrine; triethylamine / toluene / 15 h / 20 °C

2.1: tributyltin hydride / dichlorobis[tri(o-tolyl)phosphine]palladium / tetrahydrofuran / 0 - 20 °C

2.2: iodine / diethyl ether / 0.25 h / 0 °C

3.1: tributyltin hydride; lithium diisopropylamide; copper cyanide / tetrahydrofuran; diethyl ether; methanol / 0.25 h / -78 - -25 °C

3.2: 1.56 g / copper(I) chloride / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 10 h / 20 °C

4.1: 85 percent / toluene / 28 h / 205 °C

5.1: 92 percent / ethyldiisopropylamine / CH₂Cl₂ / 2 h

6.1: KHMDS / toluene / 0.03 h / -78 °C

6.2: triethylphosphite; oxygen / toluene / 1.25 h / -78 °C

7.1: lithium aluminum hydride / tetrahydrofuran / 1.25 h / 20 °C

7.2: 489 mg / NaIO₄; KH₂PO₄; Na₂HPO₄ / tetrahydrofuran; H₂O / 4.5 h / 0 - 28 °C / pH 7

With lithium aluminium tetrahydride; tri-n-butyl-tin hydride; copper(l) cyanide; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; (+)-N-methylephedrine; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo070165r

Reference yield:

: 944450-16-2
(R)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-ol

: 944450-25-3
(4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-4,4a,4b,5,8a,9,10,10a-octahydro-1-(2-(triisopropylsilyloxy)ethyl)-8,10-bis(methoxymethoxy)-4a,6-dimethylphenanthren-3(8H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: tributyltin hydride / dichlorobis[tri(o-tolyl)phosphine]palladium / tetrahydrofuran / 0 - 20 °C

1.2: iodine / diethyl ether / 0.25 h / 0 °C

2.1: tributyltin hydride; lithium diisopropylamide; copper cyanide / tetrahydrofuran; diethyl ether; methanol / 0.25 h / -78 - -25 °C

2.2: 1.56 g / copper(I) chloride / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 10 h / 20 °C

3.1: 85 percent / toluene / 28 h / 205 °C

4.1: 92 percent / ethyldiisopropylamine / CH₂Cl₂ / 2 h

5.1: KHMDS / toluene / 0.03 h / -78 °C

5.2: triethylphosphite; oxygen / toluene / 1.25 h / -78 °C

6.1: lithium aluminum hydride / tetrahydrofuran / 1.25 h / 20 °C

6.2: 489 mg / NaIO₄; KH₂PO₄; Na₂HPO₄ / tetrahydrofuran; H₂O / 4.5 h / 0 - 28 °C / pH 7

With lithium aluminium tetrahydride; tri-n-butyl-tin hydride; copper(l) cyanide; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo070165r