1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-bromobenzyl-D-glucal

Base Information

• Chemical Name: 1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-bromobenzyl-D-glucal
• CAS No.: 1247813-90-6
• Molecular Formula: C₃₅H₃₁BrO₄
• Molecular Weight: 595.533
• Mol file: 1247813-90-6.mol

Synonyms:1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-bromobenzyl-D-glucal

Chemical Property of 1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-bromobenzyl-D-glucal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-bromobenzyl-D-glucal

There total 6 articles about 1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-bromobenzyl-D-glucal 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: 85.0%

1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-D-glucal (1247813-81-5) + 1-bromomethyl-4-bromobenzene (589-15-1) → 1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-bromobenzyl-D-glucal (1247813-90-6)

Guidance literature:

1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-D-glucal; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

1-bromomethyl-4-bromobenzene; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c0cc00586j

Reference yield:

D-glucal triacetate (2873-29-2) → 1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-bromobenzyl-D-glucal (1247813-90-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium methylate; methanol / 20 °C

1.2: 20 °C

1.3: 20 °C

2.1: pyridinium chlorochromate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 2 h / -78 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 20 °C

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

5.2: 0 - 20 °C / Inert atmosphere

With methanol; n-butyllithium; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; 1,2-dichloro-ethane; mineral oil;

DOI:10.1002/chem.201402149

Reference yield:

1,5-anhydro-2-deoxy-3,4-di-O-benzyl-6-O-triisopropylsilyl-D-arabino-hex-1-enitol (196703-95-4) → 1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-bromobenzyl-D-glucal (1247813-90-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridinium chlorochromate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 20 °C

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

4.2: 0 - 20 °C / Inert atmosphere

With n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; 1,2-dichloro-ethane; mineral oil;

DOI:10.1002/chem.201402149

upstream raw materials:

1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-D-glucal

1-bromomethyl-4-bromobenzene

D-glucal triacetate

1,5-anhydro-2-deoxy-3,4-di-O-benzyl-6-O-triisopropylsilyl-D-arabino-hex-1-enitol

Refernces

• 1、 Gomez, Ana M.,Lobo, Fernando,Perez De Las Vacas, Daniel,Valverde, Serafin,Lopez, J. Cristobal. "Formation and reactivity of new Nicholas-Ferrier pyranosidic cations: Novel access to oxepanes via a 1,6-hydride shift/cyclization sequence". supporting information; experimental part. p. 6159 - 6161. Retrieved 2010/11/02.