(4aR,10aR,E)-3-benzylidene-7-((tert-butyldimethylsilyl)oxy)-4a-ethyl-1,4,4a,9,10,10a-hexahydrophenanthren-2(3H)-one

Base Information

• Chemical Name: (4aR,10aR,E)-3-benzylidene-7-((tert-butyldimethylsilyl)oxy)-4a-ethyl-1,4,4a,9,10,10a-hexahydrophenanthren-2(3H)-one
• CAS No.: 645397-09-7
• Molecular Formula: C₂₉H₃₈O₂Si
• Molecular Weight: 446.705

Synonyms:(4aR,10aR,E)-3-benzylidene-7-((tert-butyldimethylsilyl)oxy)-4a-ethyl-1,4,4a,9,10,10a-hexahydrophenanthren-2(3H)-one

Chemical Property of (4aR,10aR,E)-3-benzylidene-7-((tert-butyldimethylsilyl)oxy)-4a-ethyl-1,4,4a,9,10,10a-hexahydrophenanthren-2(3H)-one

Chemical Property:

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Technology Process of (4aR,10aR,E)-3-benzylidene-7-((tert-butyldimethylsilyl)oxy)-4a-ethyl-1,4,4a,9,10,10a-hexahydrophenanthren-2(3H)-one

There total 3 articles about (4aR,10aR,E)-3-benzylidene-7-((tert-butyldimethylsilyl)oxy)-4a-ethyl-1,4,4a,9,10,10a-hexahydrophenanthren-2(3H)-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: 49.0%

(3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one (645396-79-8) + tert-butyldimethylsilyl chloride (18162-48-6) → (4aR,10aR,E)-3-benzylidene-7-((tert-butyldimethylsilyl)oxy)-4a-ethyl-1,4,4a,9,10,10a-hexahydrophenanthren-2(3H)-one (645397-09-7)

Guidance literature:

With 1H-imidazole; In dichloromethane; for 48h;

Reference yield:

(4aR,10aR)-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one → (4aR,10aR,E)-3-benzylidene-7-((tert-butyldimethylsilyl)oxy)-4a-ethyl-1,4,4a,9,10,10a-hexahydrophenanthren-2(3H)-one (645397-09-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium ethanolate / 1 h / 20 °C / Inert atmosphere

1.2: 5 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere

With 1H-imidazole; sodium ethanolate; In dichloromethane;

DOI:10.1021/jm501601b

Reference yield:

benzaldehyde (100-52-7) → (4aR,10aR,E)-3-benzylidene-7-((tert-butyldimethylsilyl)oxy)-4a-ethyl-1,4,4a,9,10,10a-hexahydrophenanthren-2(3H)-one (645397-09-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium ethanolate / 1 h / 20 °C / Inert atmosphere

1.2: 5 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere

With 1H-imidazole; sodium ethanolate; In dichloromethane;

DOI:10.1021/jm501601b

upstream raw materials:

(3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one

tert-butyldimethylsilyl chloride

benzaldehyde

Downstream raw materials:

(2S,4aR,10aR,E)-3-benzylidene-4a-ethyl-2-(pyridin-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-2,7-diol

(4bR,7S,8aR,E)-6-benzylidene-4b-ethyl-7-hydroxy-7-(pyridin-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl 4-nitrobenzoate

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