(5Z,7E)-(3S,24R)-3,24-bis(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

Base Information

Chemical Name:(5Z,7E)-(3S,24R)-3,24-bis(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol
CAS No.:156178-28-8
Molecular Formula:C₃₉H₇₂O₄Si₂
Molecular Weight:661.169
Hs Code.:

Synonyms:(5Z,7E)-(3S,24R)-3,24-bis(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

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Chemical Property of (5Z,7E)-(3S,24R)-3,24-bis(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

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Technology Process of (5Z,7E)-(3S,24R)-3,24-bis(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

There total 15 articles about (5Z,7E)-(3S,24R)-3,24-bis(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: 33.0%

: 156178-27-7
(24R)-3β,24-bis(tert-butyldimethylsiloxy)cholesta-5,7-diene-11α,25-diol

: 156178-28-8
(5Z,7E)-(3S,24R)-3,24-bis(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

Guidance literature:: In diethyl ether; at 0 ℃; Irradiation;
DOI:10.1039/P19940000269

Reference yield:

: 142886-19-9
<17(20)Z>-pregna-5,17(20)-diene-3β,11α-diyl diacetate

: 156178-28-8
(5Z,7E)-(3S,24R)-3,24-bis(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

Guidance literature:: Multi-step reaction with 15 steps

1: 83 percent / BF₃*OEt₂ / CH₂Cl₂ / 6 h / 0 °C

2: 98 percent / H₂ / Pt/C / ethyl acetate / 0.22 h / Ambient temperature

3: 93 percent / pyridine / 16 h / 4 °C

4: 1.) LiBr, Li₂CO₃ / 1) DMF, 85 deg C, 95 min; 2) DMF, 3 h, 85 deg C

5: 98 percent / aq. KOH / methanol; tetrahydrofuran / 2 h / 60 °C

6: 87 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature

7: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / Ambient temperature

8: 92 percent / BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

9: 84 percent / Na-Hg, Na₂HPO₄, MeOH / tetrahydrofuran / 0.5 h / Ambient temperature

10: 86 percent / imidazole / dimethylformamide / 19 h / Ambient temperature

11: 93 percent / bromodimethylborane / CH₂Cl₂ / 1.33 h / -70 °C

12: 98 percent / pyridine / 5 h / Ambient temperature

13: 1.) N-bromosuccinimide, 2,2'-azoisobutyronitrile, 2.) terrabutylammonium bromide, tetrabutylammonium fluoride / 1) hexane, reflux, 12 min; 2) THF, 0 deg C, 2.5 h; 3) CH₂Cl₂, room temperature, 1 h

14: 1.) KOH, 2.) 1,1,3,3-tetramethylguanidine / 1) MeOH, room temperature, 1.5 h; 2) reflux, 70 min

15: 33 percent / diethyl ether / 0 °C / Irradiation

With pyridine; 1H-imidazole; methanol; potassium hydroxide; disodium hydrogenphosphate; N-Bromosuccinimide; n-butyllithium; sodium amalgam; 2,2'-azobis(isobutyronitrile); dimethylboron bromide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; lithium carbonate; N-ethyl-N,N-diisopropylamine; lithium bromide; N,N,N',N'-tetramethylguanidine; platinum on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1039/P19940000269

Reference yield:

: 156178-13-1
(20S)-22-hydroxy-23,24-dinorchola-5,16-diene-3β,11α-diyl diacetate

: 156178-28-8
(5Z,7E)-(3S,24R)-3,24-bis(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol

Guidance literature:: Multi-step reaction with 14 steps

1: 98 percent / H₂ / Pt/C / ethyl acetate / 0.22 h / Ambient temperature

2: 93 percent / pyridine / 16 h / 4 °C

3: 1.) LiBr, Li₂CO₃ / 1) DMF, 85 deg C, 95 min; 2) DMF, 3 h, 85 deg C

4: 98 percent / aq. KOH / methanol; tetrahydrofuran / 2 h / 60 °C

5: 87 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature

6: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / Ambient temperature

7: 92 percent / BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

8: 84 percent / Na-Hg, Na₂HPO₄, MeOH / tetrahydrofuran / 0.5 h / Ambient temperature

9: 86 percent / imidazole / dimethylformamide / 19 h / Ambient temperature

10: 93 percent / bromodimethylborane / CH₂Cl₂ / 1.33 h / -70 °C

11: 98 percent / pyridine / 5 h / Ambient temperature

12: 1.) N-bromosuccinimide, 2,2'-azoisobutyronitrile, 2.) terrabutylammonium bromide, tetrabutylammonium fluoride / 1) hexane, reflux, 12 min; 2) THF, 0 deg C, 2.5 h; 3) CH₂Cl₂, room temperature, 1 h

13: 1.) KOH, 2.) 1,1,3,3-tetramethylguanidine / 1) MeOH, room temperature, 1.5 h; 2) reflux, 70 min

14: 33 percent / diethyl ether / 0 °C / Irradiation

With pyridine; 1H-imidazole; methanol; potassium hydroxide; disodium hydrogenphosphate; N-Bromosuccinimide; n-butyllithium; sodium amalgam; 2,2'-azobis(isobutyronitrile); dimethylboron bromide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; lithium carbonate; N-ethyl-N,N-diisopropylamine; lithium bromide; N,N,N',N'-tetramethylguanidine; platinum on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1039/P19940000269