(8R,9S,10R,13S,14S)-4-(benzyloxy)-3-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthren-17(2H)-one

Base Information

Chemical Name:(8R,9S,10R,13S,14S)-4-(benzyloxy)-3-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthren-17(2H)-one
CAS No.:1338324-48-3
Molecular Formula:C₂₆H₃₂O₃
Molecular Weight:392.538
Hs Code.:

Synonyms:(8R,9S,10R,13S,14S)-4-(benzyloxy)-3-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthren-17(2H)-one

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Chemical Property of (8R,9S,10R,13S,14S)-4-(benzyloxy)-3-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthren-17(2H)-one

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Technology Process of (8R,9S,10R,13S,14S)-4-(benzyloxy)-3-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthren-17(2H)-one

There total 5 articles about (8R,9S,10R,13S,14S)-4-(benzyloxy)-3-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthren-17(2H)-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: 45.0%

: 1150096-90-4
(8R,9S,10R,13S,14S)-4-diazo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[α]phenanthrene-3,17(4H)-dione

: 100-51-6,185532-71-2
benzyl alcohol

: 1338324-48-3
(8R,9S,10R,13S,14S)-4-(benzyloxy)-3-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthren-17(2H)-one

Guidance literature:: benzyl alcohol; With Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; In 4-methyl-1,2,3-trifluorobenzene; at 20 ℃; for 0.166667h; Inert atmosphere;

(8R,9S,10R,13S,14S)-4-diazo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[α]phenanthrene-3,17(4H)-dione; In 4-methyl-1,2,3-trifluorobenzene; for 10h; regioselective reaction; Inert atmosphere;
DOI:10.1039/c2cc31973j

Reference yield:

: 94534-87-9
(8R,9S,10R,13S,14S)-6-bromo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[α]phenanthrene-3,17(6H)-dione

: 1338324-48-3
(8R,9S,10R,13S,14S)-4-(benzyloxy)-3-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthren-17(2H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: zinc / ethanol; water / 72 h / 20 °C / Inert atmosphere

2.1: 3-carbonxybenzenesulfonyl azide / acetonitrile / 0.33 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 / 4-methyl-1,2,3-trifluorobenzene / 0.17 h / 20 °C / Inert atmosphere

3.2: 10 h / Inert atmosphere

With Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; 3-carbonxybenzenesulfonyl azide; zinc; In ethanol; water; acetonitrile; 4-methyl-1,2,3-trifluorobenzene;
DOI:10.1039/c2cc31973j

Reference yield:

: 897-06-3
Androsta-1,4-diene-3,17-dione

: 1338324-48-3
(8R,9S,10R,13S,14S)-4-(benzyloxy)-3-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthren-17(2H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane; water / 4 h / 80 °C / Inert atmosphere

2.1: zinc / ethanol; water / 72 h / 20 °C / Inert atmosphere

3.1: 3-carbonxybenzenesulfonyl azide / acetonitrile / 0.33 h / 20 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

4.1: Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 / 4-methyl-1,2,3-trifluorobenzene / 0.17 h / 20 °C / Inert atmosphere

4.2: 10 h / Inert atmosphere

With N-Bromosuccinimide; Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; 3-carbonxybenzenesulfonyl azide; zinc; dibenzoyl peroxide; In tetrachloromethane; ethanol; water; acetonitrile; 4-methyl-1,2,3-trifluorobenzene;
DOI:10.1039/c2cc31973j