(2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,4-dien-8-ynal

Base Information

• Chemical Name: (2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,4-dien-8-ynal
• CAS No.: 178060-97-4
• Molecular Formula: C₃₀H₃₈O₂Si
• Molecular Weight: 458.716
• Mol file: 178060-97-4.mol

Synonyms:(2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,4-dien-8-ynal

Chemical Property of (2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,4-dien-8-ynal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,4-dien-8-ynal

There total 5 articles about (2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,4-dien-8-ynal 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: 51.0%

(2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynal (90108-26-2) + triphenylarsonium salt of bromoacetaldehyde (103698-50-6) → (2E,4R)-4-<(tert-butyldiphenylsilyl)oxy>-2-dodecen-6-ynal (116012-52-3) + (2E,4E,6E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-hexadeca-2,4,6-trien-10-ynal + (2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,4-dien-8-ynal (178060-97-4)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; diethyl ether; water; for 24h; Ambient temperature;

DOI:10.1039/p19960001057

Reference yield:

(9R,10S,11S,12R)-9,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-6,14-diyne-10,11-diol (178060-96-3) → (2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,4-dien-8-ynal (178060-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / Pb(OAc)4 / benzene / 2 h / Ambient temperature

2: K₂CO₃ / tetrahydrofuran; diethyl ether; H₂O / 24 h / Ambient temperature

With lead(IV) acetate; potassium carbonate; In tetrahydrofuran; diethyl ether; water; benzene;

DOI:10.1039/p19960001057

Reference yield:

9(R),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-10(S),11(S)-O-(1-methylethylidene)-6,14-icosadiyne-10,11-diol (119414-22-1) → (2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,4-dien-8-ynal (178060-97-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / TiCl₄, Ph₃As, HS(CH₂)3SH / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) r.t., 2 h

2: 74 percent / Pb(OAc)4 / benzene / 2 h / Ambient temperature

3: K₂CO₃ / tetrahydrofuran; diethyl ether; H₂O / 24 h / Ambient temperature

With 1.3-propanedithiol; lead(IV) acetate; triphenyl-arsane; titanium tetrachloride; potassium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; benzene;

DOI:10.1039/p19960001057

upstream raw materials:

3-Formylallyl(triphenyl)arsonium bromide

(2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynal

triphenylarsonium salt of bromoacetaldehyde

(9R,10S,11S,12R)-9,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-6,14-diyne-10,11-diol

Downstream raw materials:

[(R)-1-((1E,3E)-5-Bromo-penta-1,3-dienyl)-non-3-ynyloxy]-tert-butyl-diphenyl-silane

(2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,4-dien-8-yn-1-ol