2-Benzyloxy-1-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

Base Information

Chemical Name:2-Benzyloxy-1-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone
CAS No.:183615-75-0
Molecular Formula:C₃₄H₅₄O₄Si
Molecular Weight:554.886
Hs Code.:

2-Benzyloxy-1-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

Synonyms:2-Benzyloxy-1-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

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Chemical Property of 2-Benzyloxy-1-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

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Technology Process of 2-Benzyloxy-1-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

There total 23 articles about 2-Benzyloxy-1-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-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:

: 101053-28-5
(1S,6R)-8,8-ethylenedioxy-1-methylbicyclo[4.4.0]decan-2-one

: 183615-75-0
2-Benzyloxy-1-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

Guidance literature:: Multi-step reaction with 23 steps

1: 95 percent / Et₃N / dimethylformamide

2: 1.) O₃, 2.) Me₂S, 3.) NaBH₄

3: aq. NaIO₄ / CH₂Cl₂ / 0 °C

4: 67 percent / NaBH(OAc)3 / benzene

5: 1.) BuLi, HMPA / 1.) THF, 0 deg C, 2.) THF, RT, 9 h

6: 1.) (COCl)2, DMSO, 2.) Et₃N

7: 100 percent / BuLi / tetrahydrofuran / -78 - 0 °C

8: 75 percent / toluene / 36 h / 200 °C

9: 80 percent / 1 N aq. HCl / tetrahydrofuran; acetone

10: 72 percent / NaBH₄, CeCl₃ / ethanol

11: 74 percent / diethyl azodicarboxylate, Ph₃P, BzONa / tetrahydrofuran

12: 81 percent / (MeO)3BF₄

13: 79 percent / ethanol. NaOEt

14: 99 percent / imidazole / dimethylformamide

15: 75 percent / tetrahydrofuran / Ambient temperature

16: 89 percent / tetrabutylammonium fluoride / diethyl ether / Ambient temperature

17: 1.) Bu₃SnH, AIBN, 2.) SiO₂ / 1.) benzene

18: 90 percent / m-CPBA, NaHCO₃

19: 70 percent / BF₃*Et₂O / -78 - 20 °C

20: NH₂OH*HCl, NaOAc / ethanol

21: carbonyldiimidazole / CH₂Cl₂ / Ambient temperature

22: 1.) LiNEt₂, 2.) 2,6-di-tert-butyl-4-methylphenol / 1.) THF, 0 deg C, 30 min, 2.) THF, 30 min

23: 2.) H₂O / 1.) THF, -78 deg C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium benzoate; sodium tetrahydroborate; sodium periodate; n-butyllithium; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); 2,6-di-tert-butyl-4-methyl-phenol; (MeO)3BF₄; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; lithium diethylamide; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; sodium ethanolate; sodium acetate; silica gel; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; ozone; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,1'-carbonyldiimidazole; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1021/ja962163m

Reference yield:

: 183615-69-2
(4aS)-7t-hydroxy-2,4b-dimethyl-(4ar,4bt,8at,10at)-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-4H-phenanthren-1-one

: 183615-75-0
2-Benzyloxy-1-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / imidazole / dimethylformamide

2: 75 percent / tetrahydrofuran / Ambient temperature

3: 89 percent / tetrabutylammonium fluoride / diethyl ether / Ambient temperature

4: 1.) Bu₃SnH, AIBN, 2.) SiO₂ / 1.) benzene

5: 90 percent / m-CPBA, NaHCO₃

6: 70 percent / BF₃*Et₂O / -78 - 20 °C

7: NH₂OH*HCl, NaOAc / ethanol

8: carbonyldiimidazole / CH₂Cl₂ / Ambient temperature

9: 1.) LiNEt₂, 2.) 2,6-di-tert-butyl-4-methylphenol / 1.) THF, 0 deg C, 30 min, 2.) THF, 30 min

10: 2.) H₂O / 1.) THF, -78 deg C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); 2,6-di-tert-butyl-4-methyl-phenol; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; lithium diethylamide; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; sodium acetate; silica gel; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja962163m

Reference yield:

: (4'aS,8'aR)-4'a-Methyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-5',6'-diol

: 183615-75-0
2-Benzyloxy-1-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethanone

Guidance literature:: Multi-step reaction with 21 steps

1: aq. NaIO₄ / CH₂Cl₂ / 0 °C

2: 67 percent / NaBH(OAc)3 / benzene

3: 1.) BuLi, HMPA / 1.) THF, 0 deg C, 2.) THF, RT, 9 h

4: 1.) (COCl)2, DMSO, 2.) Et₃N

5: 100 percent / BuLi / tetrahydrofuran / -78 - 0 °C

6: 75 percent / toluene / 36 h / 200 °C

7: 80 percent / 1 N aq. HCl / tetrahydrofuran; acetone

8: 72 percent / NaBH₄, CeCl₃ / ethanol

9: 74 percent / diethyl azodicarboxylate, Ph₃P, BzONa / tetrahydrofuran

10: 81 percent / (MeO)3BF₄

11: 79 percent / ethanol. NaOEt

12: 99 percent / imidazole / dimethylformamide

13: 75 percent / tetrahydrofuran / Ambient temperature

14: 89 percent / tetrabutylammonium fluoride / diethyl ether / Ambient temperature

15: 1.) Bu₃SnH, AIBN, 2.) SiO₂ / 1.) benzene

16: 90 percent / m-CPBA, NaHCO₃

17: 70 percent / BF₃*Et₂O / -78 - 20 °C

18: NH₂OH*HCl, NaOAc / ethanol

19: carbonyldiimidazole / CH₂Cl₂ / Ambient temperature

20: 1.) LiNEt₂, 2.) 2,6-di-tert-butyl-4-methylphenol / 1.) THF, 0 deg C, 30 min, 2.) THF, 30 min

21: 2.) H₂O / 1.) THF, -78 deg C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium benzoate; sodium tetrahydroborate; sodium periodate; n-butyllithium; cerium(III) chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 2,6-di-tert-butyl-4-methyl-phenol; (MeO)3BF₄; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; lithium diethylamide; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; sodium ethanolate; sodium acetate; silica gel; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,1'-carbonyldiimidazole; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1021/ja962163m