(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methylene-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-1-[(S)-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-octahydro-indene

Base Information

• Chemical Name: (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methylene-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-1-[(S)-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-octahydro-indene
• CAS No.: 364059-48-3
• Molecular Formula: C₄₇H₈₈O₃Si₃
• Molecular Weight: 785.47

Synonyms:(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methylene-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-1-[(S)-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-octahydro-indene

Chemical Property of (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methylene-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-1-[(S)-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-octahydro-indene

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Technology Process of (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methylene-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-1-[(S)-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-octahydro-indene

There total 3 articles about (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methylene-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-1-[(S)-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-octahydro-indene 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: 42.0%

[2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (213250-64-7) + (20S)-25-[(triethylsilyl)oxy]-des-A,B-26,27-dimethylene-cholestan-8-one (364059-47-2) → (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methylene-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-1-[(S)-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-octahydro-indene (364059-48-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 20.5h;

DOI:10.1016/S0039-128X(01)00156-8

Reference yield:

triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methylene-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-1-[(S)-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-octahydro-indene (364059-48-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 46 percent / 2,6-lutidine / 1 h / 20 °C

2: 42 percent / n-BuLi / tetrahydrofuran / 20.5 h / -78 - 0 °C

With 2,6-dimethylpyridine; n-butyllithium; In tetrahydrofuran; 2: Wittig-Horner coupling;

DOI:10.1016/S0039-128X(01)00156-8

Reference yield:

(1R,3aR,7aR)-1-[(S)-4-(1-Hydroxy-cyclopentyl)-1-methyl-butyl]-7a-methyl-octahydro-inden-4-one → (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methylene-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-1-[(S)-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-octahydro-indene (364059-48-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 46 percent / 2,6-lutidine / 1 h / 20 °C

2: 42 percent / n-BuLi / tetrahydrofuran / 20.5 h / -78 - 0 °C

With 2,6-dimethylpyridine; n-butyllithium; In tetrahydrofuran; 2: Wittig-Horner coupling;

DOI:10.1016/S0039-128X(01)00156-8

upstream raw materials:

[2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

(20S)-25-[(triethylsilyl)oxy]-des-A,B-26,27-dimethylene-cholestan-8-one

triethylsilyl trifluoromethyl sulfonate

Downstream raw materials:

(20S)-1α,25-dihydroxy-26,27-dimethylene-2-methylene-19-norvitamin D₃

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