(2-{4-[2-(1-hydroxy-5-trimethylsilanyl-penta-2,4-diynyl)-thiophen-3-yl]-buta-1,3-diynyl}-benzyl)-methyl-carbamic acid tert-butyl ester

Base Information

• Chemical Name: (2-{4-[2-(1-hydroxy-5-trimethylsilanyl-penta-2,4-diynyl)-thiophen-3-yl]-buta-1,3-diynyl}-benzyl)-methyl-carbamic acid tert-butyl ester
• CAS No.: 848641-94-1
• Molecular Formula: C₂₉H₃₁NO₃SSi
• Molecular Weight: 501.722
• Mol file: 848641-94-1.mol

Synonyms:(2-{4-[2-(1-hydroxy-5-trimethylsilanyl-penta-2,4-diynyl)-thiophen-3-yl]-buta-1,3-diynyl}-benzyl)-methyl-carbamic acid tert-butyl ester

Chemical Property of (2-{4-[2-(1-hydroxy-5-trimethylsilanyl-penta-2,4-diynyl)-thiophen-3-yl]-buta-1,3-diynyl}-benzyl)-methyl-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-{4-[2-(1-hydroxy-5-trimethylsilanyl-penta-2,4-diynyl)-thiophen-3-yl]-buta-1,3-diynyl}-benzyl)-methyl-carbamic acid tert-butyl ester

There total 5 articles about (2-{4-[2-(1-hydroxy-5-trimethylsilanyl-penta-2,4-diynyl)-thiophen-3-yl]-buta-1,3-diynyl}-benzyl)-methyl-carbamic acid tert-butyl ester 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: 91.0%

1,4-bis(trimethylsilyl)-1,3-butadiyne (4526-07-2) + {2-[4-(2-formyl-thiophen-3-yl)-buta-1,3-diynyl]-benzyl}-methyl-carbamic acid tert-butyl ester (848641-99-6) → (2-{4-[2-(1-hydroxy-5-trimethylsilanyl-penta-2,4-diynyl)-thiophen-3-yl]-buta-1,3-diynyl}-benzyl)-methyl-carbamic acid tert-butyl ester (848641-94-1)

Guidance literature:

With methyllithium; lithium bromide; In diethyl ether; at -78 ℃;

DOI:10.1016/j.tetlet.2005.01.005

Reference yield:

3-bromo-2-thiophenecarboxaldehyde (930-96-1) → (2-{4-[2-(1-hydroxy-5-trimethylsilanyl-penta-2,4-diynyl)-thiophen-3-yl]-buta-1,3-diynyl}-benzyl)-methyl-carbamic acid tert-butyl ester (848641-94-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₃SnCl; diisopropylamine / 20 °C

1.2: [PdCl₂(PPh₃)2] / toluene / 80 °C

2.1: 91 percent / MeLi; LiBr / diethyl ether / -78 °C

With tributyltin chloride; methyllithium; diisopropylamine; lithium bromide; In diethyl ether; 1.2: Stille coupling;

DOI:10.1016/j.tetlet.2005.01.005

Reference yield:

(N-tert-butoxycarbonyl-N-methyl)-2-iodobenzylamine (341970-35-2) → (2-{4-[2-(1-hydroxy-5-trimethylsilanyl-penta-2,4-diynyl)-thiophen-3-yl]-buta-1,3-diynyl}-benzyl)-methyl-carbamic acid tert-butyl ester (848641-94-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 97 percent / [PdCl₂(PPh₃)2] / toluene / 110 °C

2.1: K₂CO₃ / methanol / 0 °C

3.1: Bu₃SnCl; diisopropylamine / 20 °C

3.2: [PdCl₂(PPh₃)2] / toluene / 80 °C

4.1: 91 percent / MeLi; LiBr / diethyl ether / -78 °C

With tributyltin chloride; methyllithium; potassium carbonate; diisopropylamine; lithium bromide; bis-triphenylphosphine-palladium(II) chloride; In methanol; diethyl ether; toluene; 1.1: Stille coupling / 3.2: Stille coupling;

DOI:10.1016/j.tetlet.2005.01.005

upstream raw materials:

1,4-bis(trimethylsilyl)-1,3-butadiyne

{2-[4-(2-formyl-thiophen-3-yl)-buta-1,3-diynyl]-benzyl}-methyl-carbamic acid tert-butyl ester

3-bromo-2-thiophenecarboxaldehyde

(N-tert-butoxycarbonyl-N-methyl)-2-iodobenzylamine