1-bromo-7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-yne

Base Information

• Chemical Name: 1-bromo-7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-yne
• CAS No.: 158719-01-8
• Molecular Formula: C₃₁H₃₉BrOSi
• Molecular Weight: 535.64
• Mol file: 158719-01-8.mol

Synonyms:1-bromo-7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-yne

Chemical Property of 1-bromo-7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-yne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-bromo-7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-yne

There total 5 articles about 1-bromo-7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-yne 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: 98.0%

tert-Butyl-[(Z)-(R)-((1E,3E)-1-hexa-1,3-dien-5-ynyl)-non-3-enyloxy]-diphenyl-silane (157394-82-6) → 1-bromo-7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-yne (158719-01-8)

Guidance literature:

With N-Bromosuccinimide; silver nitrate; In acetone; at 24 ℃; for 1h;

DOI:10.1021/ja00091a004

Reference yield:

Toluene-4-sulfonic acid (2R,3S)-5-hydroxy-2-((Z)-oct-2-enyl)-tetrahydro-furan-3-yl ester (135236-80-5,135236-82-7) → 1-bromo-7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-yne (158719-01-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) HMPA, NaN(SiMe₃)2 / 1.) THF, from -78 deg C to RT, 1.5 h, 2.) THF, from -78 to -30 deg C, 4 h

2: 97 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 24 °C

3: 95 percent / pyridine, AgNO₃ / CH₂Cl₂ / 6 h / Ambient temperature

4: 98 percent / AgNO₃, NBS / acetone / 1 h / 24 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; N-Bromosuccinimide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; silver nitrate; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/ja00091a004

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 1-bromo-7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-yne (158719-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine, AgNO₃ / CH₂Cl₂ / 6 h / Ambient temperature

2: 98 percent / AgNO₃, NBS / acetone / 1 h / 24 °C

With pyridine; N-Bromosuccinimide; silver nitrate; In dichloromethane; acetone;

DOI:10.1021/ja00091a004

upstream raw materials:

tert-Butyl-[(Z)-(R)-((1E,3E)-1-hexa-1,3-dien-5-ynyl)-non-3-enyloxy]-diphenyl-silane

Toluene-4-sulfonic acid (2R,3S)-5-hydroxy-2-((Z)-oct-2-enyl)-tetrahydro-furan-3-yl ester

tert-butylchlorodiphenylsilane

(3E,5E,9Z)-(R)-Pentadeca-3,5,9-trien-1-yn-7-ol

Downstream raw materials:

2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran

2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran

3(S),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-5(S)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetranoic δ-lactone

3(R),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-5(S)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetranoic δ-lactone