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

Base Information

• Chemical Name: (1S,3R,20S)-20-(4-hydroxy-4-methylpentanoyloxy)-9,10-secopregna-5Z,7E,10⁽¹⁹⁾-trien-1,3-diol
• CAS No.: 889452-88-4
• Molecular Formula: C₂₇H₄₂O₅
• Molecular Weight: 446.627

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

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

Chemical Property:

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

There total 5 articles about (1S,3R,20S)-20-(4-hydroxy-4-methylpentanoyloxy)-9,10-secopregna-5Z,7E,10⁽¹⁹⁾-trien-1,3-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:

(1S,3R,20S)-20-(4-triethylsilyloxy-4-methylpentanoyloxy)-1,3-bis(tert-butyldimethylsilyloxy)-9,10-secopregna-5Z,7E,10(19)-triene (889453-41-2) → (1S,3R,20S)-20-(4-hydroxy-4-methylpentanoyloxy)-9,10-secopregna-5Z,7E,10(19)-trien-1,3-diol (889452-88-4)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

Reference yield:

(1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)pregna-5,7-dien-20-ol → (1S,3R,20S)-20-(4-hydroxy-4-methylpentanoyloxy)-9,10-secopregna-5Z,7E,10(19)-trien-1,3-diol (889452-88-4)

Guidance literature:

Multi-step reaction with 3 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

3.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

With 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran;

Reference yield:

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 (103909-74-6) → (1S,3R,20S)-20-(4-hydroxy-4-methylpentanoyloxy)-9,10-secopregna-5Z,7E,10(19)-trien-1,3-diol (889452-88-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 3.12 h / 0 °C / UV-irradiation; Heating / reflux

2: dmap / benzene / 0.5 h / 20 °C

3: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 °C

With dmap; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; benzene;

upstream raw materials:

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

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

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

4-triethylsilyloxy-4-methylpentanoic acid

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