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

Base Information

Chemical Name:tert-butyl ((E)-4-(1S,2S,4R)-4-(2-(2,2-dimethoxyethyl)-4-methyl-1-(triethylsilyloxy)cyclopentyl)-6-phenoxyhex-4-enyloxy)diphenylsilane
CAS No.:1384122-51-3
Molecular Formula:C₄₄H₆₆O₅Si₂
Molecular Weight:731.176
Hs Code.:

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

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

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

There total 13 articles about tert-butyl ((E)-4-(1S,2S,4R)-4-(2-(2,2-dimethoxyethyl)-4-methyl-1-(triethylsilyloxy)cyclopentyl)-6-phenoxyhex-4-enyloxy)diphenylsilane 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: 73.0%

: C₄₂H₆₀O₄Si₂

: 149-73-5
trimethyl orthoformate

: 1384122-51-3
tert-butyl ((E)-4-(1S,2S,4R)-4-(2-(2,2-dimethoxyethyl)-4-methyl-1-(triethylsilyloxy)cyclopentyl)-6-phenoxyhex-4-enyloxy)diphenylsilane

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 23 ℃; for 5h; Inert atmosphere;
DOI:10.1021/jo300872y

Reference yield:

: 1229041-57-9
(1S,2S,4R)-2-(2-hydroxyethyl)-4-methylcyclopentanol

: 1384122-51-3
tert-butyl ((E)-4-(1S,2S,4R)-4-(2-(2,2-dimethoxyethyl)-4-methyl-1-(triethylsilyloxy)cyclopentyl)-6-phenoxyhex-4-enyloxy)diphenylsilane

Guidance literature:: Multi-step reaction with 6 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

4.1: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere

5.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 23 °C / Inert atmosphere

6.1: pyridinium p-toluenesulfonate / dichloromethane / 5 h / 23 °C / Inert atmosphere

With 2,6-dimethylpyridine; oxalyl dichloride; sec.-butyllithium; pyridinium p-toluenesulfonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 5.1: |Swern Oxidation;
DOI:10.1021/jo300872y

Reference yield:

: 56487-70-8
(3aS,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

: 1384122-51-3
tert-butyl ((E)-4-(1S,2S,4R)-4-(2-(2,2-dimethoxyethyl)-4-methyl-1-(triethylsilyloxy)cyclopentyl)-6-phenoxyhex-4-enyloxy)diphenylsilane

Guidance literature:: Multi-step reaction with 8 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

6.1: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere

7.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 23 °C / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / dichloromethane / 5 h / 23 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; dimethylsulfide; sec.-butyllithium; pyridinium p-toluenesulfonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 7.1: |Swern Oxidation;
DOI:10.1021/jo300872y