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

Base Information

Chemical Name:methyl (2Z,5R,7S,8E)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-9-phenylnona-2,8-dienoate
CAS No.:1374348-41-0
Molecular Formula:C₂₂H₃₄O₄Si
Molecular Weight:390.595
Hs Code.:

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

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Chemical Property of methyl (2Z,5R,7S,8E)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-9-phenylnona-2,8-dienoate

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Technology Process of methyl (2Z,5R,7S,8E)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-9-phenylnona-2,8-dienoate

There total 5 articles about methyl (2Z,5R,7S,8E)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-9-phenylnona-2,8-dienoate 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:

: 1374348-52-3
C₁₉H₃₀O₃Si

: 88738-78-7
bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

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

Guidance literature:: bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.333333h;

C₁₉H₃₀O₃Si; In tetrahydrofuran; at -78 ℃;
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

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

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

: 1228293-95-5
C₁₇H₂₆O₂Si

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

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 0.17 h / 0 °C / Inert atmosphere

1.3: 1 h / -78 °C / Inert atmosphere

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

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

3.2: -78 °C

With titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene; 3.2: Still-Gennari reaction;
DOI:10.1016/j.tetlet.2012.02.073