[(1R,2S,4aS,4bS,6R,8S,8aR,9S,9aS)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-9-(4-methoxymethoxymethyl-phenoxy)-2,4,4b,6,8-pentamethyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-2-yl]-methanol

Base Information

• Chemical Name: [(1R,2S,4aS,4bS,6R,8S,8aR,9S,9aS)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-9-(4-methoxymethoxymethyl-phenoxy)-2,4,4b,6,8-pentamethyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-2-yl]-methanol
• CAS No.: 864152-07-8
• Molecular Formula: C₄₅H₆₂O₅Si
• Molecular Weight: 711.07

Synonyms:[(1R,2S,4aS,4bS,6R,8S,8aR,9S,9aS)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-9-(4-methoxymethoxymethyl-phenoxy)-2,4,4b,6,8-pentamethyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-2-yl]-methanol

Chemical Property of [(1R,2S,4aS,4bS,6R,8S,8aR,9S,9aS)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-9-(4-methoxymethoxymethyl-phenoxy)-2,4,4b,6,8-pentamethyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-2-yl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2S,4aS,4bS,6R,8S,8aR,9S,9aS)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-9-(4-methoxymethoxymethyl-phenoxy)-2,4,4b,6,8-pentamethyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-2-yl]-methanol

There total 23 articles about [(1R,2S,4aS,4bS,6R,8S,8aR,9S,9aS)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-9-(4-methoxymethoxymethyl-phenoxy)-2,4,4b,6,8-pentamethyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-2-yl]-methanol 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:

(3aS,4S,6R,7aR)-4,6,7a-Trimethyl-3a,4,5,6,7,7a-hexahydro-inden-1-one (871329-34-9) → [(1R,2S,4aS,4bS,6R,8S,8aR,9S,9aS)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-9-(4-methoxymethoxymethyl-phenoxy)-2,4,4b,6,8-pentamethyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-2-yl]-methanol (864152-07-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 97 percent / tetrahydrofuran / 5 h / -78 - -23 °C

2.1: 77 percent / aq. H₂SO₄ / tetrahydrofuran / 24 h / 0 - 20 °C

3.1: NaH / tetrahydrofuran / 7 h / Heating

3.2: CAN; NaHCO₃ / acetonitrile / 0.33 h / -23 °C

3.3: 70 percent / aq. Dess-Martin periodinane / acetonitrile; CH₂Cl₂ / 39 h / 20 °C

4.1: 95 percent / KHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

5.1: 83 percent / toluene / 10 h / Heating

6.1: 91 percent / LiBH₄ / tetrahydrofuran; methanol / 24 h / 0 - 20 °C

7.1: TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

8.1: imidazole / dimethylformamide / 1 h / 20 °C

9.1: LDA; TMSCl / tetrahydrofuran / 3 h / -78 °C

9.2: Pd(OAc)2 / acetonitrile / 10 h / 50 °C

10.1: TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

11.1: 2,6-lutidine / CH₂Cl₂ / 4 h / -78 - -45 °C

12.1: 84 percent / Cu(II)-salicylidene-iminato complex / tetrahydrofuran / 44 h / -45 °C

13.1: MeLi / tetrahydrofuran / 2 h / -78 - 20 °C

13.2: 86 percent / tetrahydrofuran / 16 h / -78 °C

14.1: 95 percent / Pd(PPh₃)4 / tetrahydrofuran / 28 h / 0 - 20 °C

15.1: Et₃N; DMAP / CH₂Cl₂ / 4 h / -78 - -45 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium borohydride; chloro-trimethyl-silane; sulfuric acid; tetrabutyl ammonium fluoride; methyllithium; potassium hexamethylsilazane; sodium hydride; triethylamine; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Cu(II)-salicylidene-iminato; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-2005-871549

Reference yield:

(3aR,4S,6R,7aR)-4,6,7a-Trimethyl-octahydro-inden-1-one (864151-96-2) → [(1R,2S,4aS,4bS,6R,8S,8aR,9S,9aS)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-9-(4-methoxymethoxymethyl-phenoxy)-2,4,4b,6,8-pentamethyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-2-yl]-methanol (864152-07-8)

Guidance literature:

Multi-step reaction with 17 steps

1.1: LDA / tetrahydrofuran / 3 h / -78 °C

1.2: tetrahydrofuran

2.1: allyl carbonate / Pd(OAc)2 / acetonitrile / Heating

3.1: 97 percent / tetrahydrofuran / 5 h / -78 - -23 °C

4.1: 77 percent / aq. H₂SO₄ / tetrahydrofuran / 24 h / 0 - 20 °C

5.1: NaH / tetrahydrofuran / 7 h / Heating

5.2: CAN; NaHCO₃ / acetonitrile / 0.33 h / -23 °C

5.3: 70 percent / aq. Dess-Martin periodinane / acetonitrile; CH₂Cl₂ / 39 h / 20 °C

6.1: 95 percent / KHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

7.1: 83 percent / toluene / 10 h / Heating

8.1: 91 percent / LiBH₄ / tetrahydrofuran; methanol / 24 h / 0 - 20 °C

9.1: TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

10.1: imidazole / dimethylformamide / 1 h / 20 °C

11.1: LDA; TMSCl / tetrahydrofuran / 3 h / -78 °C

11.2: Pd(OAc)2 / acetonitrile / 10 h / 50 °C

12.1: TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

13.1: 2,6-lutidine / CH₂Cl₂ / 4 h / -78 - -45 °C

14.1: 84 percent / Cu(II)-salicylidene-iminato complex / tetrahydrofuran / 44 h / -45 °C

15.1: MeLi / tetrahydrofuran / 2 h / -78 - 20 °C

15.2: 86 percent / tetrahydrofuran / 16 h / -78 °C

16.1: 95 percent / Pd(PPh₃)4 / tetrahydrofuran / 28 h / 0 - 20 °C

17.1: Et₃N; DMAP / CH₂Cl₂ / 4 h / -78 - -45 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium borohydride; chloro-trimethyl-silane; diallylcarbonate; sulfuric acid; tetrabutyl ammonium fluoride; methyllithium; potassium hexamethylsilazane; sodium hydride; triethylamine; lithium diisopropyl amide; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Cu(II)-salicylidene-iminato; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1055/s-2005-871549

Reference yield:

(1R,3aR,4S,6R,7aR)-4,6,7a-Trimethyl-octahydro-inden-1-ol (864151-95-1) → [(1R,2S,4aS,4bS,6R,8S,8aR,9S,9aS)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-9-(4-methoxymethoxymethyl-phenoxy)-2,4,4b,6,8-pentamethyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-2-yl]-methanol (864152-07-8)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 93 percent / (COCl)2; DMSO; Et₃N / 1 h / -78 - 0 °C

2.1: LDA / tetrahydrofuran / 3 h / -78 °C

2.2: tetrahydrofuran

3.1: allyl carbonate / Pd(OAc)2 / acetonitrile / Heating

4.1: 97 percent / tetrahydrofuran / 5 h / -78 - -23 °C

5.1: 77 percent / aq. H₂SO₄ / tetrahydrofuran / 24 h / 0 - 20 °C

6.1: NaH / tetrahydrofuran / 7 h / Heating

6.2: CAN; NaHCO₃ / acetonitrile / 0.33 h / -23 °C

6.3: 70 percent / aq. Dess-Martin periodinane / acetonitrile; CH₂Cl₂ / 39 h / 20 °C

7.1: 95 percent / KHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

8.1: 83 percent / toluene / 10 h / Heating

9.1: 91 percent / LiBH₄ / tetrahydrofuran; methanol / 24 h / 0 - 20 °C

10.1: TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

11.1: imidazole / dimethylformamide / 1 h / 20 °C

12.1: LDA; TMSCl / tetrahydrofuran / 3 h / -78 °C

12.2: Pd(OAc)2 / acetonitrile / 10 h / 50 °C

13.1: TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

14.1: 2,6-lutidine / CH₂Cl₂ / 4 h / -78 - -45 °C

15.1: 84 percent / Cu(II)-salicylidene-iminato complex / tetrahydrofuran / 44 h / -45 °C

16.1: MeLi / tetrahydrofuran / 2 h / -78 - 20 °C

16.2: 86 percent / tetrahydrofuran / 16 h / -78 °C

17.1: 95 percent / Pd(PPh₃)4 / tetrahydrofuran / 28 h / 0 - 20 °C

18.1: Et₃N; DMAP / CH₂Cl₂ / 4 h / -78 - -45 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium borohydride; chloro-trimethyl-silane; oxalyl dichloride; diallylcarbonate; sulfuric acid; tetrabutyl ammonium fluoride; methyllithium; potassium hexamethylsilazane; sodium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Cu(II)-salicylidene-iminato; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Swern oxidation;

DOI:10.1055/s-2005-871549

upstream raw materials:

C₃₇H₆₀O₅Si

tert-butylchlorodiphenylsilane

(3aS,4S,6R,7aR)-4,6,7a-Trimethyl-3a,4,5,6,7,7a-hexahydro-inden-1-one

(3aR,4S,6R,7aR)-4,6,7a-Trimethyl-octahydro-inden-1-one

Downstream raw materials:

{4-[(1S,3R,4aS,4bS,7S,8R,8aS,9S,9aR)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-1,3,4a,5,7-pentamethyl-7-vinyl-2,3,4,4a,4b,7,8,8a,9,9a-decahydro-1H-fluoren-9-yloxy]-phenyl}-methanol

tert-Butyl-[(1R,2S,4aS,4bS,6R,8S,8aR,9S,9aS)-9-(4-methoxymethoxymethyl-phenoxy)-2,4,4b,6,8-pentamethyl-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-1-ylmethoxy]-diphenyl-silane

(1R,2S,4aS,4bS,6R,8S,8aR,9S,9aS)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-9-(4-methoxymethoxymethyl-phenoxy)-2,4,4b,6,8-pentamethyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-2-carbaldehyde

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