(Z)-6α,7β-(diacetoxy)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-pregn-17(20)-ene

Base Information

• Chemical Name: (Z)-6α,7β-(diacetoxy)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-pregn-17(20)-ene
• CAS No.: 537674-16-1
• Molecular Formula: C₄₁H₅₆O₅Si
• Molecular Weight: 656.978

Synonyms:(Z)-6α,7β-(diacetoxy)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-pregn-17(20)-ene

Chemical Property of (Z)-6α,7β-(diacetoxy)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-pregn-17(20)-ene

Chemical Property:

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Technology Process of (Z)-6α,7β-(diacetoxy)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-pregn-17(20)-ene

There total 11 articles about (Z)-6α,7β-(diacetoxy)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-pregn-17(20)-ene 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: 96.0%

acetic anhydride (108-24-7) + (Z)-3β-[(tert-butyldiphenylsilyl)oxy]-6α,7β-[(methylethylidene)-bis-oxy]-5α-pregn-17(20)-ene (537674-14-9) → (Z)-6α,7β-(diacetoxy)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-pregn-17(20)-ene (537674-16-1)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/S0040-4020(03)00108-X

Reference yield:

dehydroepiandrosterone (53-43-0) → (Z)-6α,7β-(diacetoxy)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-pregn-17(20)-ene (537674-16-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 95 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 2 h / 20 °C

2.1: 100 percent / triethyl orthoformate; p-TsOH*H₂O / CH₂Cl₂ / 20 °C

3.1: 81 percent / CrO₃; dimethylpyrazole / CH₂Cl₂ / 4 h / -20 °C

4.1: 81 percent / CeCl₃; NaBH₄ / ethanol; tetrahydrofuran / 1 h / 20 °C

5.1: 98 percent / DMAP; pyridine / CH₂Cl₂ / 4 h / 20 °C

6.1: BH₃*SMe₂ / tetrahydrofuran / 0 - 20 °C

6.2: 72 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O; ethanol / 2 h / 0 °C

7.1: 84 percent / Pd(CH₃CN)2Cl₂ / H₂O; acetone / 20 - 40 °C

8.1: 93 percent / pyridinium p-toluenesulfonate / 20 °C

9.1: tBuOK / tetrahydrofuran / 0.17 h

9.2: 92 percent / tetrahydrofuran / 3 h / Heating

10.1: 96 percent / pyridine; DMAP / CH₂Cl₂ / 48 h / 20 °C

With pyridine; 1,3-dimethyl-1H-pyrazole; chromium(VI) oxide; dmap; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; cerium(III) chloride; dimethylsulfide borane complex; potassium tert-butylate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; orthoformic acid triethyl ester; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; 9.2: Wittig olefination;

DOI:10.1016/S0040-4020(03)00108-X

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (Z)-6α,7β-(diacetoxy)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-pregn-17(20)-ene (537674-16-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 95 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 2 h / 20 °C

2.1: 100 percent / triethyl orthoformate; p-TsOH*H₂O / CH₂Cl₂ / 20 °C

3.1: 81 percent / CrO₃; dimethylpyrazole / CH₂Cl₂ / 4 h / -20 °C

4.1: 81 percent / CeCl₃; NaBH₄ / ethanol; tetrahydrofuran / 1 h / 20 °C

5.1: 98 percent / DMAP; pyridine / CH₂Cl₂ / 4 h / 20 °C

6.1: BH₃*SMe₂ / tetrahydrofuran / 0 - 20 °C

6.2: 72 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O; ethanol / 2 h / 0 °C

7.1: 84 percent / Pd(CH₃CN)2Cl₂ / H₂O; acetone / 20 - 40 °C

8.1: 93 percent / pyridinium p-toluenesulfonate / 20 °C

9.1: tBuOK / tetrahydrofuran / 0.17 h

9.2: 92 percent / tetrahydrofuran / 3 h / Heating

10.1: 96 percent / pyridine; DMAP / CH₂Cl₂ / 48 h / 20 °C

With pyridine; 1,3-dimethyl-1H-pyrazole; chromium(VI) oxide; dmap; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; cerium(III) chloride; dimethylsulfide borane complex; potassium tert-butylate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; orthoformic acid triethyl ester; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; 9.2: Wittig olefination;

DOI:10.1016/S0040-4020(03)00108-X

upstream raw materials:

acetic anhydride

(Z)-3β-[(tert-butyldiphenylsilyl)oxy]-6α,7β-[(methylethylidene)-bis-oxy]-5α-pregn-17(20)-ene

dehydroepiandrosterone

tert-butylchlorodiphenylsilane

Downstream raw materials:

6α,7β-(diacetoxy)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-23,24-bisnorchol-16-en-22-ol

Acetic acid (3S,5S,6R,7R,8R,9S,10R,13S,14S)-7-acetoxy-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-17-((S)-1-methyl-2-oxo-ethyl)-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl ester

acetic acid 7-acetoxy-3-(tert-butyl-diphenyl-silanyloxy)-17-(2-furan-3-yl-2-hydroxy-1-methyl-ethyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl ester

acetic acid 7-acetoxy-3-(tert-butyl-diphenyl-silanyloxy)-17-(2-furan-3-yl-2-hydroxy-1-methyl-ethyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl ester

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