(3β,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol diacetate

Base Information

Chemical Name:(3β,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol diacetate
CAS No.:157522-95-7
Molecular Formula:C₃₁H₄₂O₄
Molecular Weight:478.672
Hs Code.:

Synonyms:(3β,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol diacetate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol diacetate

Chemical Property:

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Technology Process of (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol diacetate

There total 15 articles about (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol diacetate 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:

: 784-04-3
9-acetylanthracene

: 10287-53-3
ethyl p-dimethyaminolbenzoate

: 157522-94-6
(3β)-Cholesta-5,7,16-trien-23-yne-3,25-diol diacetate

: 157522-95-7
(3β,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol diacetate

Guidance literature:: With hydrogenchloride; In hexane; tert-butyl methyl ether; ethyl acetate;

Reference yield:

: 53-43-0
dehydroepiandrosterone

: 157522-95-7
(3β,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol diacetate

Guidance literature:: Multi-step reaction with 12 steps

1: 99.9 percent / BF₃*Et₂O / CH₂Cl₂ / 4 h / 25 °C

2: 1,3-dibromo-5,5-dimethylhydantoin / cyclohexane / 0.5 h / Heating

3: 1.0 M n-Bu₄NF / tetrahydrofuran

4: 25percent NaOMe / methanol

5: imidazole / CH₂Cl₂ / Ambient temperature

6: 93.7 percent / t-BuOK / toluene / 1.) r.t., 1 h, 2.) r.t., overnight

7: Me₂AlCl / hexane / 0.5 h / -40 °C

8: NaH / tetrahydrofuran / 1.) 5 - 15 deg C, 2 h, 2.) 10 - 20 deg C, 2 h

9: n-Bu₃SnH, AIBN / hexane / 2 h / Heating

10: aq. n-Bu₄NF / tetrahydrofuran / 18 h / Ambient temperature

11: 89.8 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; dmap; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; dimethylaluminum chloride; sodium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; toluene;
DOI:10.1021/jo00108a055

Reference yield:

: 853-23-6
prasterone acetate

: 157522-95-7
(3β,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol diacetate

Guidance literature:: Multi-step reaction with 11 steps

1: 1,3-dibromo-5,5-dimethylhydantoin / cyclohexane / 0.5 h / Heating

2: 1.0 M n-Bu₄NF / tetrahydrofuran

3: 25percent NaOMe / methanol

4: imidazole / CH₂Cl₂ / Ambient temperature

5: 93.7 percent / t-BuOK / toluene / 1.) r.t., 1 h, 2.) r.t., overnight

6: Me₂AlCl / hexane / 0.5 h / -40 °C

7: NaH / tetrahydrofuran / 1.) 5 - 15 deg C, 2 h, 2.) 10 - 20 deg C, 2 h

8: n-Bu₃SnH, AIBN / hexane / 2 h / Heating

9: aq. n-Bu₄NF / tetrahydrofuran / 18 h / Ambient temperature

10: 89.8 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; dmap; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; dimethylaluminum chloride; sodium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; toluene;
DOI:10.1021/jo00108a055