(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

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-fluorene-2-carbaldehyde
CAS No.:864152-16-9
Molecular Formula:C₄₅H₆₀O₅Si
Molecular Weight:709.054
Hs Code.:

(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

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-fluorene-2-carbaldehyde

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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-fluorene-2-carbaldehyde

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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-fluorene-2-carbaldehyde

There total 24 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-fluorene-2-carbaldehyde 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: 95.0%

: 864152-07-8
[(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

: 864152-16-9
(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-fluorene-2-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; at -78 - 0 ℃; for 1h;
DOI:10.1055/s-2005-871549

Reference yield:

: 871329-34-9
(3aS,4S,6R,7aR)-4,6,7a-Trimethyl-3a,4,5,6,7,7a-hexahydro-inden-1-one

: 864152-16-9
(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-fluorene-2-carbaldehyde

Guidance literature:: Multi-step reaction with 16 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

16.1: 95 percent / (COCl)2; DMSO; Et₃N / 1 h / -78 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium borohydride; chloro-trimethyl-silane; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; methyllithium; potassium hexamethylsilazane; sodium hydride; dimethyl sulfoxide; 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:

: 864151-96-2
(3aR,4S,6R,7aR)-4,6,7a-Trimethyl-octahydro-inden-1-one

: 864152-16-9
(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-fluorene-2-carbaldehyde

Guidance literature:: Multi-step reaction with 18 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

18.1: 95 percent / (COCl)2; DMSO; Et₃N / 1 h / -78 - 0 °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;
DOI:10.1055/s-2005-871549