(1S,3R,20S)-20-(4-triethylsilyloxy-4-methylpentanoyloxy)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10⁽¹⁹⁾-triene

Base Information

• Chemical Name: (1S,3R,20S)-20-(4-triethylsilyloxy-4-methylpentanoyloxy)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10⁽¹⁹⁾-triene
• CAS No.: 889453-41-2
• Molecular Formula: C₄₅H₈₄O₅Si₃
• Molecular Weight: 789.415

Synonyms:(1S,3R,20S)-20-(4-triethylsilyloxy-4-methylpentanoyloxy)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10⁽¹⁹⁾-triene

Chemical Property of (1S,3R,20S)-20-(4-triethylsilyloxy-4-methylpentanoyloxy)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10⁽¹⁹⁾-triene

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Technology Process of (1S,3R,20S)-20-(4-triethylsilyloxy-4-methylpentanoyloxy)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10⁽¹⁹⁾-triene

There total 5 articles about (1S,3R,20S)-20-(4-triethylsilyloxy-4-methylpentanoyloxy)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,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:

C19H27Cl3O4Si + (1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10(19)-trien-20-ol (204520-81-0) → (1S,3R,20S)-20-(4-triethylsilyloxy-4-methylpentanoyloxy)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10(19)-triene (889453-41-2)

Guidance literature:

With dmap; In benzene; at 20 ℃; for 0.5h;

Reference yield:

(1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10(19)-trien-20-ol (204520-81-0) + 4-triethylsilyloxy-4-methylpentanoic acid (383397-31-7) → (1S,3R,20S)-20-(4-triethylsilyloxy-4-methylpentanoyloxy)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10(19)-triene (889453-41-2)

Guidance literature:

4-triethylsilyloxy-4-methylpentanoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 0.5h;

(1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10⁽¹⁹⁾-trien-20-ol; With dmap; In benzene; at 20 ℃; for 0.5h; Inert atmosphere;

Reference yield:

(1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)pregna-5,7-dien-20-ol → (1S,3R,20S)-20-(4-triethylsilyloxy-4-methylpentanoyloxy)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10(19)-triene (889453-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 3.5 h / Inert atmosphere; Cooling with ice; Microwave irradiation; Reflux

2.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.5 h / 20 °C

2.2: 0.5 h / 20 °C / Inert atmosphere

With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran;

upstream raw materials:

(1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10⁽¹⁹⁾-trien-20-ol

4-triethylsilyloxy-4-methylpentanoic acid

1-[1,3-bis-(tert-butyldimethylsilanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanol

Downstream raw materials:

(1S,3R,20S)-20-(4-hydroxy-4-methylpentanoyloxy)-9,10-secopregna-5Z,7E,10⁽¹⁹⁾-trien-1,3-diol

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