1-[(3R,5S,8S,9S,10S,11S,13S,14S,16S,17S)-3,11-bis-(benzyloxy)-17-bromo-16-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-one

Base Information

• Chemical Name: 1-[(3R,5S,8S,9S,10S,11S,13S,14S,16S,17S)-3,11-bis-(benzyloxy)-17-bromo-16-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-one
• CAS No.: 1578266-60-0
• Molecular Formula: C₃₆H₄₇BrO₄
• Molecular Weight: 623.671

Synonyms:1-[(3R,5S,8S,9S,10S,11S,13S,14S,16S,17S)-3,11-bis-(benzyloxy)-17-bromo-16-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-one

Chemical Property of 1-[(3R,5S,8S,9S,10S,11S,13S,14S,16S,17S)-3,11-bis-(benzyloxy)-17-bromo-16-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(3R,5S,8S,9S,10S,11S,13S,14S,16S,17S)-3,11-bis-(benzyloxy)-17-bromo-16-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-one

There total 10 articles about 1-[(3R,5S,8S,9S,10S,11S,13S,14S,16S,17S)-3,11-bis-(benzyloxy)-17-bromo-16-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-one 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: 75.0%

1-[(3R,5S,8S,9S,10S,11S,13S,14S)-3,11-bis(benzyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-one (1578266-59-7) → 1-[(3R,5S,8S,9S,10S,11S,13S,14S,16S,17S)-3,11-bis-(benzyloxy)-17-bromo-16-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-one (1578266-60-0)

Guidance literature:

With N-bromoacetamide; In tetrahydrofuran; water; acetone; at 20 ℃; for 6h; Darkness;

DOI:10.1021/jm401799j

Reference yield:

HYDROCORTISONE (50-23-7) → 1-[(3R,5S,8S,9S,10S,11S,13S,14S,16S,17S)-3,11-bis-(benzyloxy)-17-bromo-16-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-one (1578266-60-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: hydrogenchloride / water / 4 h / 20 °C / Inert atmosphere

1.2: 4 h / 20 °C / Inert atmosphere

2.1: ammonia; lithium / tetrahydrofuran; tert-butyl alcohol / 3 h / -33 °C / Inert atmosphere

3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 4.5 h / 0 °C / Inert atmosphere; Reflux

5.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere; Reflux

5.2: 36 h / Inert atmosphere; Reflux

6.1: hydrogen fluoride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

7.1: p-toluenesulfonic acid monohydrate / toluene / 24 h / 20 °C / Inert atmosphere

8.1: potassium acetate / toluene; dimethyl sulfoxide / 6 h / 120 °C / Inert atmosphere

9.1: ethylmagnesium bromide / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere; Cooling with ice

9.2: silica gel supported NaIO₄ / 20 °C / Inert atmosphere

10.1: N-bromoacetamide / acetone; water; tetrahydrofuran / 6 h / 20 °C / Darkness

With hydrogenchloride; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; hydrogen fluoride; ethylmagnesium bromide; p-toluenesulfonic acid monohydrate; ammonia; potassium acetate; lithium; sodium hydride; triphenylphosphine; N-bromoacetamide; In tetrahydrofuran; water; dimethyl sulfoxide; acetone; toluene; mineral oil; tert-butyl alcohol;

DOI:10.1021/jm401799j

Reference yield:

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydrodispiro[cyclopenta[a]phenanthrene-17,4′-[1,3]dioxolane-5′,4″-[1,3]-dioxolan]-3(2H)-one (807-05-6) → 1-[(3R,5S,8S,9S,10S,11S,13S,14S,16S,17S)-3,11-bis-(benzyloxy)-17-bromo-16-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-one (1578266-60-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: ammonia; lithium / tetrahydrofuran; tert-butyl alcohol / 3 h / -33 °C / Inert atmosphere

2.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 4.5 h / 0 °C / Inert atmosphere; Reflux

4.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere; Reflux

4.2: 36 h / Inert atmosphere; Reflux

5.1: hydrogen fluoride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

6.1: p-toluenesulfonic acid monohydrate / toluene / 24 h / 20 °C / Inert atmosphere

7.1: potassium acetate / toluene; dimethyl sulfoxide / 6 h / 120 °C / Inert atmosphere

8.1: ethylmagnesium bromide / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere; Cooling with ice

8.2: silica gel supported NaIO₄ / 20 °C / Inert atmosphere

9.1: N-bromoacetamide / acetone; water; tetrahydrofuran / 6 h / 20 °C / Darkness

With lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; hydrogen fluoride; ethylmagnesium bromide; p-toluenesulfonic acid monohydrate; ammonia; potassium acetate; lithium; sodium hydride; triphenylphosphine; N-bromoacetamide; In tetrahydrofuran; water; dimethyl sulfoxide; acetone; toluene; mineral oil; tert-butyl alcohol;

DOI:10.1021/jm401799j

upstream raw materials:

HYDROCORTISONE

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydrodispiro[cyclopenta[a]phenanthrene-17,4′-[1,3]dioxolane-5′,4″-[1,3]-dioxolan]-3(2H)-one

(3S,5S,8S,9S,10S,11S,13S,14S)-10,13-dimethylhexadecahydrodispiro[cyclopenta[a]phenanthrene-17,4′-[1,3]-dioxolane-5′,4″-[1,3]dioxolane]-3,11-diol

(3R,5S,8S,9S,10S,11S,13S,14S)-11-hydroxy-10,13-dimethylhexadecahydrodispiro[cyclopenta[a]phenanthrene-17,4′-[1,3]dioxolane-5′,4″-[1,3]dioxolan]-3-yl benzoate

Downstream raw materials:

1-[(3R,5S,8S,9S,10S,11S,13S,14S,16S,17R)-3,11-bis-(benzyloxy)-16-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-one

C₄₃H₆₀O₅

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