1-((1R,4aR,4bS,6R,8aS,9R,10aS)-7-(3-(4-methoxybenzyloxy)propyl)-1,4,4a,4b,5,6,8a,9,10,10a-decahydro-9-hydroxy-8-(2-(triisopropylsilyloxy)ethyl)-1-(methoxymethoxy)-3,4b-dimethylphenanthren-6-yl)ethanone

Base Information

• Chemical Name: 1-((1R,4aR,4bS,6R,8aS,9R,10aS)-7-(3-(4-methoxybenzyloxy)propyl)-1,4,4a,4b,5,6,8a,9,10,10a-decahydro-9-hydroxy-8-(2-(triisopropylsilyloxy)ethyl)-1-(methoxymethoxy)-3,4b-dimethylphenanthren-6-yl)ethanone
• CAS No.: 944450-39-9
• Molecular Formula: C₄₂H₆₈O₇Si
• Molecular Weight: 713.083

Synonyms:1-((1R,4aR,4bS,6R,8aS,9R,10aS)-7-(3-(4-methoxybenzyloxy)propyl)-1,4,4a,4b,5,6,8a,9,10,10a-decahydro-9-hydroxy-8-(2-(triisopropylsilyloxy)ethyl)-1-(methoxymethoxy)-3,4b-dimethylphenanthren-6-yl)ethanone

Chemical Property of 1-((1R,4aR,4bS,6R,8aS,9R,10aS)-7-(3-(4-methoxybenzyloxy)propyl)-1,4,4a,4b,5,6,8a,9,10,10a-decahydro-9-hydroxy-8-(2-(triisopropylsilyloxy)ethyl)-1-(methoxymethoxy)-3,4b-dimethylphenanthren-6-yl)ethanone

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

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Useful:

Technology Process of 1-((1R,4aR,4bS,6R,8aS,9R,10aS)-7-(3-(4-methoxybenzyloxy)propyl)-1,4,4a,4b,5,6,8a,9,10,10a-decahydro-9-hydroxy-8-(2-(triisopropylsilyloxy)ethyl)-1-(methoxymethoxy)-3,4b-dimethylphenanthren-6-yl)ethanone

There total 12 articles about 1-((1R,4aR,4bS,6R,8aS,9R,10aS)-7-(3-(4-methoxybenzyloxy)propyl)-1,4,4a,4b,5,6,8a,9,10,10a-decahydro-9-hydroxy-8-(2-(triisopropylsilyloxy)ethyl)-1-(methoxymethoxy)-3,4b-dimethylphenanthren-6-yl)ethanone 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:

2-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]ethanol (944450-14-0) → 1-((1R,4aR,4bS,6R,8aS,9R,10aS)-7-(3-(4-methoxybenzyloxy)propyl)-1,4,4a,4b,5,6,8a,9,10,10a-decahydro-9-hydroxy-8-(2-(triisopropylsilyloxy)ethyl)-1-(methoxymethoxy)-3,4b-dimethylphenanthren-6-yl)ethanone (944450-39-9)

Guidance literature:

Multi-step reaction with 5 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 / dichlorobis(tris(o-tolyl)phosphine)palladium / tetrahydrofuran / 0 - 20 °C

4.2: DMSO; sulfur trioxide-pyridine complex; ethyldiisopropylamine / CH₂Cl₂ / 0.67 h / -40 - -10 °C

4.3: 358 mg / copper(I) chloride / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 3 h / 20 °C

5.1: toluene / 16 h / 200 °C

With tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; zinc trifluoromethanesulfonate; (+)-N-methylephedrine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; dichloromethane; toluene; 1.1: Parikh-Doering oxidation / 4.2: Parikh-Doering oxidation;

DOI:10.1021/jo070165r

Reference yield:

(1R,5R,6S)-6-(2-hydroxyethyl)-3-methyl-5-(prop-1-en-2-yl)cyclohex-2-enol (944450-09-3) → 1-((1R,4aR,4bS,6R,8aS,9R,10aS)-7-(3-(4-methoxybenzyloxy)propyl)-1,4,4a,4b,5,6,8a,9,10,10a-decahydro-9-hydroxy-8-(2-(triisopropylsilyloxy)ethyl)-1-(methoxymethoxy)-3,4b-dimethylphenanthren-6-yl)ethanone (944450-39-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 78 percent / pyridine / 0.5 h / 0 °C

2.1: 96 percent / ethyldiisopropylamine / CH₂Cl₂ / 0 - 20 °C

3.1: 97 percent / DIBAL-H / CH₂Cl₂; hexane / 1.5 h / -78 °C

4.1: 98 percent / sulfur trioxide-pyridine complex; ethyldiisopropylamine; DMSO / CH₂Cl₂ / 0.67 h / -30 - -15 °C

5.1: 78 percent / Zn(OTf)2; (+)-N-methylephedrine; triethylamine / toluene / 15 h / 20 °C

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

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

7.1: tributyltin hydride / dichlorobis(tris(o-tolyl)phosphine)palladium / tetrahydrofuran / 0 - 20 °C

7.2: DMSO; sulfur trioxide-pyridine complex; ethyldiisopropylamine / CH₂Cl₂ / 0.67 h / -40 - -10 °C

7.3: 358 mg / copper(I) chloride / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 3 h / 20 °C

8.1: toluene / 16 h / 200 °C

With pyridine; tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; (+)-N-methylephedrine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; hexane; dichloromethane; toluene; 4.1: Parikh-Doering oxidation / 7.2: Parikh-Doering oxidation;

DOI:10.1021/jo070165r

Reference yield:

2-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetaldehyde (944450-15-1) → 1-((1R,4aR,4bS,6R,8aS,9R,10aS)-7-(3-(4-methoxybenzyloxy)propyl)-1,4,4a,4b,5,6,8a,9,10,10a-decahydro-9-hydroxy-8-(2-(triisopropylsilyloxy)ethyl)-1-(methoxymethoxy)-3,4b-dimethylphenanthren-6-yl)ethanone (944450-39-9)

Guidance literature:

Multi-step reaction with 4 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 / dichlorobis(tris(o-tolyl)phosphine)palladium / tetrahydrofuran / 0 - 20 °C

3.2: DMSO; sulfur trioxide-pyridine complex; ethyldiisopropylamine / CH₂Cl₂ / 0.67 h / -40 - -10 °C

3.3: 358 mg / copper(I) chloride / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 3 h / 20 °C

4.1: toluene / 16 h / 200 °C

With tri-n-butyl-tin hydride; zinc trifluoromethanesulfonate; (+)-N-methylephedrine; triethylamine; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; toluene; 3.2: Parikh-Doering oxidation;

DOI:10.1021/jo070165r

upstream raw materials:

(7R,3E,5E)-4-(3-(4-methoxybenzyloxy)propyl)-7-hydroxy-5-(2-(triisopropylsilyloxy)ethyl)-8-((1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl)octa-3,5-dien-2-one

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

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

(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

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