(5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

Base Information

Chemical Name:(5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol
CAS No.:132787-57-6
Molecular Formula:C₃₃H₅₈O₃Si
Molecular Weight:530.907
Hs Code.:

Synonyms:(5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

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Chemical Property of (5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

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Technology Process of (5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

There total 20 articles about (5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol 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%

: C₃₉H₇₄O₃Si₃

: 132787-57-6
(5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

Guidance literature:: With oxalic acid; In methanol;
DOI:10.1016/j.jsbmb.2020.105638

Reference yield:

: 518337-35-4
(3S,8S,9S,10R,11R,13S,14S)-17-Eth-(Z)-ylidene-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,11-diol

: 132787-57-6
(5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

Guidance literature:: Multi-step reaction with 16 steps

1: pyridine, 4-(dimethylamino)pyridine (DMAP) / tetrahydrofuran / 1 h / Ambient temperature

2: 91 percent / EtAlCl₂ / CH₂Cl₂; hexane / 2.5 h / Ambient temperature

3: 96 percent / H₂ / 5percent Pt-C / ethyl acetate / 0.83 h / Ambient temperature

4: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating

5: 1) i-Pr₂NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h

6: 91 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / Ambient temperature

7: 90 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 5 h / Ambient temperature

8: 1) PhLi / 1) cyclohexane, Et₂O, THF, r.t., 30 min, 2) THF, r.t., 30 min

9: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature

10: 1) Hg(OAc)2, 2) NaBH₄, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min

11: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

12: 97 percent / pyridine / 5 h / Ambient temperature

14: 96 percent / 10percent aq. KOH / methanol; tetrahydrofuran / 1.5 h / Ambient temperature

15: 89 percent / 1,1,3,3-tetramethylguanidine / 2 h / Heating

16: 1) Et₂O, irradiation, 0 deg C, 120 sec, 2) THF, hexane, r.t., darkness, 7 d

With pyridine; 1H-imidazole; hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; mercury(II) diacetate; hydrogen; ethylaluminum dichloride; phenyllithium; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; N,N,N',N'-tetramethylguanidine; platinum on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

: 39663-17-7
3β,11α-dihydroxyandrost-5-en-17-one

: 132787-57-6
(5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

Guidance literature:: Multi-step reaction with 17 steps

1: 1) t-BuOK / 1) THF, 55 deg C (bath temp.), 1 h, 2) THF, reflux, 1 h

2: pyridine, 4-(dimethylamino)pyridine (DMAP) / tetrahydrofuran / 1 h / Ambient temperature

3: 91 percent / EtAlCl₂ / CH₂Cl₂; hexane / 2.5 h / Ambient temperature

4: 96 percent / H₂ / 5percent Pt-C / ethyl acetate / 0.83 h / Ambient temperature

5: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating

6: 1) i-Pr₂NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h

7: 91 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / Ambient temperature

8: 90 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 5 h / Ambient temperature

9: 1) PhLi / 1) cyclohexane, Et₂O, THF, r.t., 30 min, 2) THF, r.t., 30 min

10: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature

11: 1) Hg(OAc)2, 2) NaBH₄, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min

12: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

13: 97 percent / pyridine / 5 h / Ambient temperature

15: 96 percent / 10percent aq. KOH / methanol; tetrahydrofuran / 1.5 h / Ambient temperature

16: 89 percent / 1,1,3,3-tetramethylguanidine / 2 h / Heating

17: 1) Et₂O, irradiation, 0 deg C, 120 sec, 2) THF, hexane, r.t., darkness, 7 d

With pyridine; 1H-imidazole; hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; potassium tert-butylate; mercury(II) diacetate; hydrogen; ethylaluminum dichloride; phenyllithium; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; N,N,N',N'-tetramethylguanidine; platinum on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;