(1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene

Base Information

• Chemical Name: (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene
• CAS No.: 112910-41-5
• Molecular Formula: C₃₉H₆₈O₃Si₂
• Molecular Weight: 641.138

Synonyms:(1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene

Chemical Property of (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene

Chemical Property:

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98% ^*data from raw suppliers

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Technology Process of (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene

There total 16 articles about (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene 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:

(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene (112849-26-0,134523-61-8,910133-69-6,910133-34-5) → (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene (112910-41-5,134523-61-8,910133-69-6,910133-34-5)

Guidance literature:

With anthracene; triethylamine; In toluene; at 20 ℃; for 1h; Irradiation;

DOI:10.1016/S0040-4020(01)86903-9

Reference yield:

Cyclopropyl methyl ketone (765-43-5) → (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene (112910-41-5,134523-61-8,910133-69-6,910133-34-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / bromine / methanol / 0.5 h / Ambient temperature

2: 84 percent

3: 86 percent / 2N sodium hydroxide / H₂O; CH₂Cl₂

5: N-methylmorpholine N-oxide, selenium dioxide

6: imidazole / dimethylformamide

7: 55 percent / NaBH₄, CeCl₃*6H₂O / methanol / further reag.: (S)-BINAL-H

8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; selenium(IV) oxide; cerium(III) chloride; anthracene; bromine; 4-methylmorpholine N-oxide; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)86903-9

Reference yield:

2-bromo-1-cyclopropylethan-1-one (69267-75-0) → (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(R)-cycloprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene (112910-41-5,134523-61-8,910133-69-6,910133-34-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent

2: 86 percent / 2N sodium hydroxide / H₂O; CH₂Cl₂

4: N-methylmorpholine N-oxide, selenium dioxide

5: imidazole / dimethylformamide

6: 55 percent / NaBH₄, CeCl₃*6H₂O / methanol / further reag.: (S)-BINAL-H

7: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; selenium(IV) oxide; cerium(III) chloride; anthracene; 4-methylmorpholine N-oxide; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)86903-9

upstream raw materials:

(1S,3R,3'R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene

Cyclopropyl methyl ketone

2-bromo-1-cyclopropylethan-1-one

1-cyclopropyl-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one

Downstream raw materials:

20(R)-(3'(R)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-1(S),3(R)-dihydroxy-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene

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