(R)-5-[(1S,3R,9S,10R,13R,14R,17R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,2-difluoro-3-hydroxy-hexanoic acid ethyl ester

Base Information

Chemical Name:(R)-5-[(1S,3R,9S,10R,13R,14R,17R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,2-difluoro-3-hydroxy-hexanoic acid ethyl ester
CAS No.:150283-03-7
Molecular Formula:C₃₉H₆₈F₂O₅Si₂
Molecular Weight:711.134
Hs Code.:

(R)-5-[(1S,3R,9S,10R,13R,14R,17R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,2-difluoro-3-hydroxy-hexanoic acid ethyl ester

Synonyms:(R)-5-[(1S,3R,9S,10R,13R,14R,17R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,2-difluoro-3-hydroxy-hexanoic acid ethyl ester

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Chemical Property of (R)-5-[(1S,3R,9S,10R,13R,14R,17R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,2-difluoro-3-hydroxy-hexanoic acid ethyl ester

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Technology Process of (R)-5-[(1S,3R,9S,10R,13R,14R,17R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,2-difluoro-3-hydroxy-hexanoic acid ethyl ester

There total 1 articles about (R)-5-[(1S,3R,9S,10R,13R,14R,17R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,2-difluoro-3-hydroxy-hexanoic acid ethyl ester 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:

: 20998-18-9
1α,3β-dihydroxy-androst-5-en-17-one

: 150283-03-7
(R)-5-[(1S,3R,9S,10R,13R,14R,17R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,2-difluoro-3-hydroxy-hexanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 89 percent / imidazole / dimethylformamide / 0.5 h / Ambient temperature

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 100 percent / tert-BuOK / tetrahydrofuran / 4 h / Heating

4: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 0.08 h / Ambient temperature

5: 95 percent / H₂ / 5percent Pt/C / ethanol / Ambient temperature

6: 1.) N-bromosuccinimide (NBS), NaHCO₃, 2.) n-Bu₄NBr / 1.) n-hexane, reflux, 1 h, 2.) THF, 0 deg C, 15 min

7: n-Bu₄NF / tetrahydrofuran / 3.5 h / 0 °C

8: 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / Ambient temperature

9: dimethylformamide / 1.5 h / 80 °C

10: diisobutylaluminum hydride (DIBAL-H) / hexane; diethyl ether / 0.25 h / 0 °C

11: 1.) Zn / 1.) THF, reflux, 2 min, 2.) THF, reflux, 15 min

With 1H-imidazole; 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; zinc; platinum on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.40.1120

Reference yield:

: 150283-03-7
(R)-5-[(1S,3R,9S,10R,13R,14R,17R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,2-difluoro-3-hydroxy-hexanoic acid ethyl ester

: 72696-49-2
24F₂-1,25(OH)2-D₃

Guidance literature:: Multi-step reaction with 5 steps

1: 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 1 h / Ambient temperature

2: azobisisobutyronitrile (AIBN), n-Bu₃SnH / toluene / 1 h / Heating

3: 98 percent / diethyl ether / 0.5 h / 0 °C

4: 98 percent / n-Bu₄NF / tetrahydrofuran / 1.) RT, overnight, 2.) 70 deg C, 1 h

5: 1.) ether, 0 deg C, irrad., 6 min, 2.) EtOH, reflux, 1 h

With dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1248/cpb.40.1120