(1S,2S,4R)-1-((E)-6-(tert-butyldiphenylsilyloxy)-1-phenoxyhex-2-en-3-yl)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanol

Base Information

• Chemical Name: (1S,2S,4R)-1-((E)-6-(tert-butyldiphenylsilyloxy)-1-phenoxyhex-2-en-3-yl)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanol
• CAS No.: 1229041-75-1
• Molecular Formula: C₄₂H₆₂O₄Si₂
• Molecular Weight: 687.123

Synonyms:(1S,2S,4R)-1-((E)-6-(tert-butyldiphenylsilyloxy)-1-phenoxyhex-2-en-3-yl)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanol

Chemical Property of (1S,2S,4R)-1-((E)-6-(tert-butyldiphenylsilyloxy)-1-phenoxyhex-2-en-3-yl)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,4R)-1-((E)-6-(tert-butyldiphenylsilyloxy)-1-phenoxyhex-2-en-3-yl)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanol

There total 9 articles about (1S,2S,4R)-1-((E)-6-(tert-butyldiphenylsilyloxy)-1-phenoxyhex-2-en-3-yl)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanol 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: 90.0%

(2S,4R)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanone (1229041-58-0) + (E)-tert-butyl(4-iodo-6-phenoxyhex-4-enyloxy)diphenylsilane (1229041-59-1) → (1S,2S,4R)-1-((E)-6-(tert-butyldiphenylsilyloxy)-1-phenoxyhex-2-en-3-yl)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanol (1229041-75-1)

Guidance literature:

(E)-tert-butyl(4-iodo-6-phenoxyhex-4-enyloxy)diphenylsilane; With (2-methylpropyl)lithium; In tetrahydrofuran; cyclohexane; at -78 - -50 ℃;

With cerium(III) chloride; lithium chloride; In tetrahydrofuran; cyclohexane; at -78 ℃;

(2S,4R)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanone; In tetrahydrofuran; cyclohexane; at -78 - 23 ℃;

DOI:10.1021/ja103666n

Reference yield:

(3aS,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (56487-70-8) → (1S,2S,4R)-1-((E)-6-(tert-butyldiphenylsilyloxy)-1-phenoxyhex-2-en-3-yl)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanol (1229041-75-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper(I) bromide dimethylsulfide complex; dimethylsulfide / tetrahydrofuran / -20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux; Inert atmosphere

3.1: 2,6-dimethylpyridine / dichloromethane / -78 °C / Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / Inert atmosphere

5.1: sec.-butyllithium / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

5.2: 0.5 h / -78 °C / Inert atmosphere

5.3: 12 h / -78 - 23 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; copper(I) bromide dimethylsulfide complex; dimethylsulfide; sec.-butyllithium; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo300872y

Reference yield:

(1S,2S,4R)-2-(2-hydroxyethyl)-4-methylcyclopentanol (1229041-57-9) → (1S,2S,4R)-1-((E)-6-(tert-butyldiphenylsilyloxy)-1-phenoxyhex-2-en-3-yl)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanol (1229041-75-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / dichloromethane / -78 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / Inert atmosphere

3.1: sec.-butyllithium / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

3.3: 12 h / -78 - 23 °C / Inert atmosphere

With 2,6-dimethylpyridine; sec.-butyllithium; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo300872y

upstream raw materials:

(2S,4R)-4-methyl-2-(2-(triethylsilyloxy)ethyl)cyclopentanone

(E)-tert-butyl(4-iodo-6-phenoxyhex-4-enyloxy)diphenylsilane

(1S,2S,4R)-2-(2-hydroxyethyl)-4-methylcyclopentanol

(3aS,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

Downstream raw materials:

tert-butyl((E)-4-((1S,2S,4R)-4-methyl-1-(triethylsilyloxy)-2-(2-(triethylsilyloxy)ethyl)cyclopentyl)-6-phenoxyhex-4-enyloxy)diphenylsilane

tert-butyl ((E)-4-(1S,2S,4R)-4-(2-(2,2-dimethoxyethyl)-4-methyl-1-(triethylsilyloxy)cyclopentyl)-6-phenoxyhex-4-enyloxy)diphenylsilane

(3S,7aS)-3a-(3-(tert-butyldiphenylsilyloxy)propyl)-6-methyl-2-methylene-3-(phenoxymethyl)hexahydro-1H-inden-4(2H)-one

C₃₇H₄₆O₃Si

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