(R)-6-((S,E)-2-(tert-butyldimethylsilyloxy)-4-phenylbut-3-enyl)-5,6-dihydro-2H-pyran-2-one

Base Information

Chemical Name:(R)-6-((S,E)-2-(tert-butyldimethylsilyloxy)-4-phenylbut-3-enyl)-5,6-dihydro-2H-pyran-2-one
CAS No.:1374348-47-6
Molecular Formula:C₂₁H₃₀O₃Si
Molecular Weight:358.553
Hs Code.:

Synonyms:(R)-6-((S,E)-2-(tert-butyldimethylsilyloxy)-4-phenylbut-3-enyl)-5,6-dihydro-2H-pyran-2-one

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Chemical Property of (R)-6-((S,E)-2-(tert-butyldimethylsilyloxy)-4-phenylbut-3-enyl)-5,6-dihydro-2H-pyran-2-one

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Technology Process of (R)-6-((S,E)-2-(tert-butyldimethylsilyloxy)-4-phenylbut-3-enyl)-5,6-dihydro-2H-pyran-2-one

There total 6 articles about (R)-6-((S,E)-2-(tert-butyldimethylsilyloxy)-4-phenylbut-3-enyl)-5,6-dihydro-2H-pyran-2-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: 92.0%

: 1374348-41-0
methyl (2Z,5R,7S,8E)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-9-phenylnona-2,8-dienoate

: 1374348-47-6
(R)-6-((S,E)-2-(tert-butyldimethylsilyloxy)-4-phenylbut-3-enyl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: With camphor-10-sulfonic acid; In benzene; at 20 ℃; for 1h;
DOI:10.1016/j.tetlet.2012.02.073

Reference yield:

: 1374348-46-5
(S,E)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-4-en-1-one

: 1374348-47-6
(R)-6-((S,E)-2-(tert-butyldimethylsilyloxy)-4-phenylbut-3-enyl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C

2.1: titanium tetrachloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

2.2: 0.17 h / 0 °C / Inert atmosphere

2.3: 1 h / -78 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C

4.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C

4.2: -78 °C

5.1: camphor-10-sulfonic acid / benzene / 1 h / 20 °C

With camphor-10-sulfonic acid; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene; benzene; 4.2: Still-Gennari reaction;
DOI:10.1016/j.tetlet.2012.02.073

Reference yield:

: 1374348-42-1
(3S,5S,E)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-phenylhept-6-en-1-one

: 1374348-47-6
(R)-6-((S,E)-2-(tert-butyldimethylsilyloxy)-4-phenylbut-3-enyl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C

2.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C

2.2: -78 °C

3.1: camphor-10-sulfonic acid / benzene / 1 h / 20 °C

With camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene; benzene; 2.2: Still-Gennari reaction;
DOI:10.1016/j.tetlet.2012.02.073