(-)-(1β,9β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicrasan-12-one

Base Information

Chemical Name:(-)-(1β,9β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicrasan-12-one
CAS No.:149494-65-5
Molecular Formula:C₃₈H₅₄O₅Si
Molecular Weight:618.929
Hs Code.:

Synonyms:(-)-(1β,9β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicrasan-12-one

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Chemical Property of (-)-(1β,9β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicrasan-12-one

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Technology Process of (-)-(1β,9β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicrasan-12-one

There total 40 articles about (-)-(1β,9β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicrasan-12-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: 81.0%

: 130575-34-7,149400-11-3
(3R,3aS,5S,6aR,7aS,8R,11R,11aS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-3a,4,5,6a,7,7a,8,9,10,11,11a,11c-dodecahydro-3H-6-oxa-benzo[de]anthracen-2-one

: 130575-35-8,130694-37-0,149494-65-5,149494-66-6,149494-68-8
(3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-2-one

Guidance literature:: With ammonia; lithium; tert-butyl alcohol; at -78 ℃;
DOI:10.1021/ja00181a079

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

: 149494-65-5
(-)-(1β,9β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicrasan-12-one

Guidance literature:: Multi-step reaction with 13 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

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; 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

: 149494-65-5
(-)-(1β,9β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicrasan-12-one

Guidance literature:: Multi-step reaction with 12 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

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; In tetrahydrofuran; 1,4-dioxane; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja00067a025