(3S,3aR,5R,6aS,7aR,8S,11S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene

Base Information

Chemical Name:(3S,3aR,5R,6aS,7aR,8S,11S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene
CAS No.:149400-40-8
Molecular Formula:C₄₁H₆₂O₅Si₂
Molecular Weight:691.111
Hs Code.:

(3S,3aR,5R,6aS,7aR,8S,11S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene

Synonyms:(3S,3aR,5R,6aS,7aR,8S,11S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene

Suppliers and Price of (3S,3aR,5R,6aS,7aR,8S,11S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (3S,3aR,5R,6aS,7aR,8S,11S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (3S,3aR,5R,6aS,7aR,8S,11S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene

There total 30 articles about (3S,3aR,5R,6aS,7aR,8S,11S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene 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:

: 21531-34-0,73211-71-9,94198-85-3,148683-75-4
(+)-1β-acetoxy-1,2,3,7,8,8a-hexahydro-8aβ-methyl-6(5H)-naphthalenone ethylene ketal

: 149400-40-8
(3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene

Guidance literature:: Multi-step reaction with 14 steps

1: LiAlH₄ / diethyl ether

2: 1.) Zn-Cu / 1.) ether, reflux, 30 min, 2.) ether, reflux, 2 h

3: 1.) NaH, 2.) tetra-n-butylammonium iodide, 3.) 70percent HClO₄

4: 80 percent / NH₃, Li / 2-methyl-propan-2-ol; tetrahydrofuran / 1.5 h / -78 °C

5: 95 percent / NaH, EtOH / benzene / 3 h

6: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, acetic acid / dioxane / 1.62 h

7: 73 percent / LiClO₄ / ethyl acetate / 43 h / Ambient temperature

8: 1.) NaBH₄, 2.) aq. HCl / 1.) THF, H₂O, 0 deg C, 50 min, 2.) THF, from 0 deg C to RT, overnight

9: 1.) imidazole / 1.) DMF, RT, 15 min, 2.) DMF, RT, 42 h

10: i-Bu₂AlH / tetrahydrofuran; toluene / 2 h / -78 °C

11: aq. HCl / tetrahydrofuran / 16 h / Ambient temperature

12: 1.) diborane, 2.) aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, a) 0 deg C, 30 min, b) RT, 4 h, 2.) THF, RT, overnight

13: sodium acetate, Celite, pyridinium chlorochromate, 4 Angstroem molecular sieves / CH₂Cl₂ / a) 0 deg C, 30 min, b) RT, 1 h 15 min

14: 1.) LDA / 1.) THF, hexane, a) -78 deg C, 1 h, b) 0 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 30 min, b) 0 deg C, 30 min

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; perchloric acid; ethanol; 4 A molecular sieve; Celite; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; tetra-(n-butyl)ammonium iodide; lithium; copper; sodium hydride; diisobutylaluminium hydride; acetic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diborane; zinc; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja00067a025

Reference yield:

: 125517-91-1
(+)-1,2,3,7,8,8a-hexahydro-1β-hydroxy-8aβ-methyl-6(5H)-naphthalenone ethylene ketal

: 149400-40-8
(3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) Zn-Cu / 1.) ether, reflux, 30 min, 2.) ether, reflux, 2 h

2: 1.) NaH, 2.) tetra-n-butylammonium iodide, 3.) 70percent HClO₄

3: 80 percent / NH₃, Li / 2-methyl-propan-2-ol; tetrahydrofuran / 1.5 h / -78 °C

4: 95 percent / NaH, EtOH / benzene / 3 h

5: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, acetic acid / dioxane / 1.62 h

6: 73 percent / LiClO₄ / ethyl acetate / 43 h / Ambient temperature

7: 1.) NaBH₄, 2.) aq. HCl / 1.) THF, H₂O, 0 deg C, 50 min, 2.) THF, from 0 deg C to RT, overnight

8: 1.) imidazole / 1.) DMF, RT, 15 min, 2.) DMF, RT, 42 h

9: i-Bu₂AlH / tetrahydrofuran; toluene / 2 h / -78 °C

10: aq. HCl / tetrahydrofuran / 16 h / Ambient temperature

11: 1.) diborane, 2.) aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, a) 0 deg C, 30 min, b) RT, 4 h, 2.) THF, RT, overnight

12: sodium acetate, Celite, pyridinium chlorochromate, 4 Angstroem molecular sieves / CH₂Cl₂ / a) 0 deg C, 30 min, b) RT, 1 h 15 min

13: 1.) LDA / 1.) THF, hexane, a) -78 deg C, 1 h, b) 0 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 30 min, b) 0 deg C, 30 min

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; perchloric acid; ethanol; 4 A molecular sieve; Celite; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; tetra-(n-butyl)ammonium iodide; lithium; copper; sodium hydride; diisobutylaluminium hydride; acetic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diborane; zinc; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja00067a025

Reference yield:

: 100348-93-4
(R)-Wieland-Miescher ketone

: 149400-40-8
(3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-2-trimethylsilanyloxy-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene

Guidance literature:: Multi-step reaction with 17 steps

1: NaBH₄ / methanol; CH₂Cl₂ / -78 °C

2: iPr₂NEt, DMAP / CH₂Cl₂ / 0 °C

3: p-TsOH / benzene / Heating

4: LiAlH₄ / diethyl ether

5: 1.) Zn-Cu / 1.) ether, reflux, 30 min, 2.) ether, reflux, 2 h

6: 1.) NaH, 2.) tetra-n-butylammonium iodide, 3.) 70percent HClO₄

7: 80 percent / NH₃, Li / 2-methyl-propan-2-ol; tetrahydrofuran / 1.5 h / -78 °C

8: 95 percent / NaH, EtOH / benzene / 3 h

9: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, acetic acid / dioxane / 1.62 h

10: 73 percent / LiClO₄ / ethyl acetate / 43 h / Ambient temperature

11: 1.) NaBH₄, 2.) aq. HCl / 1.) THF, H₂O, 0 deg C, 50 min, 2.) THF, from 0 deg C to RT, overnight

12: 1.) imidazole / 1.) DMF, RT, 15 min, 2.) DMF, RT, 42 h

13: i-Bu₂AlH / tetrahydrofuran; toluene / 2 h / -78 °C

14: aq. HCl / tetrahydrofuran / 16 h / Ambient temperature

15: 1.) diborane, 2.) aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, a) 0 deg C, 30 min, b) RT, 4 h, 2.) THF, RT, overnight

16: sodium acetate, Celite, pyridinium chlorochromate, 4 Angstroem molecular sieves / CH₂Cl₂ / a) 0 deg C, 30 min, b) RT, 1 h 15 min

17: 1.) LDA / 1.) THF, hexane, a) -78 deg C, 1 h, b) 0 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 30 min, b) 0 deg C, 30 min

With 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; perchloric acid; ethanol; 4 A molecular sieve; Celite; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; tetra-(n-butyl)ammonium iodide; lithium; copper; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diborane; zinc; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja00067a025