Phosphonium, [3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]triphenyl-, iodide

Base Information

• Chemical Name: Phosphonium, [3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]triphenyl-, iodide
• CAS No.: 88157-27-1
• Molecular Formula: C27H36OPSi.I
• Molecular Weight: 562.546
• Mol file: 88157-27-1.mol

Synonyms:

Chemical Property of Phosphonium, [3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]triphenyl-, iodide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phosphonium, [3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]triphenyl-, iodide

There total 6 articles about Phosphonium, [3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]triphenyl-, iodide 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: 86.0%

1-iodo-3-(tert-butyldimethylsilyloxy)propane (78878-05-4) + triphenylphosphine (603-35-0) → (3-((tert-butyldimetylisilyl)oxy)propyl)triphenylphosphonium iodide (88157-27-1)

Guidance literature:

In tetrahydrofuran; for 96h; Heating;

DOI:10.1021/jo0014663

Reference yield:

3-tert-butyldimethylsilyloxy-1-propanol (73842-99-6) → (3-((tert-butyldimetylisilyl)oxy)propyl)triphenylphosphonium iodide (88157-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; 1H-imidazole; iodine / acetonitrile; diethyl ether / 1.17 h / 0 - 25 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / 24 h / 80 °C / Inert atmosphere

With 1H-imidazole; iodine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In diethyl ether; acetonitrile;

DOI:10.1021/jo4006156

Reference yield:

1-(t-Butyldimethylsilyloxy)-3-chloro-propane (89031-82-3) → (3-((tert-butyldimetylisilyl)oxy)propyl)triphenylphosphonium iodide (88157-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium iodide / acetone / 48 h / Heating

2: 86 percent / tetrahydrofuran / 96 h / Heating

With sodium iodide; In tetrahydrofuran; acetone;

DOI:10.1021/jo0014663

upstream raw materials:

tert-butyldimethylsilyl chloride

triphenylphosphine

1-chloro-3-hydroxypropane

1-iodo-3-(tert-butyldimethylsilyloxy)propane

Downstream raw materials:

C₁₉H₃₂O₃Si

(E)-3-{2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-hex-3-enyl]-4-methoxy-phenyl}-prop-2-en-1-ol

(E)-3-{2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-hex-3-enyl]-4-methoxy-phenyl}-acrylic acid ethyl ester

[3-(tert-butyl-dimethyl-silanyloxy)-propylidene]-triphenyl-λ⁵-phosphane

Refernces

• 1、 Nagasawa, Shota,Sasano, Yusuke,Iwabuchi, Yoshiharu. "Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts". supporting information. p. 13189 - 13194. Retrieved 2016/10/30.
• 2、 Merlic,Aldrich,Albaneze-Walker,Saghatelian,Mammen. "Total synthesis of the calphostins: Application of Fischer carbene complexes and thermodynamic control of atropisomers". . p. 1297 - 1309. Retrieved 2007/10/03.