(5R,15R)-5,6,14,15-tetrabenzyl-3,17-dioxa-6,14,23,24-tetraazatricyclo[17.3.1.1(8,12)]tetracosa-1⁽²³⁾,8,10,12⁽²⁴⁾,19,21-hexaene

Base Information

• Chemical Name: (5R,15R)-5,6,14,15-tetrabenzyl-3,17-dioxa-6,14,23,24-tetraazatricyclo[17.3.1.1(8,12)]tetracosa-1⁽²³⁾,8,10,12⁽²⁴⁾,19,21-hexaene
• CAS No.: 1329682-36-1
• Molecular Formula: C₄₆H₄₈N₄O₂
• Molecular Weight: 688.913
• Mol file: 1329682-36-1.mol

Synonyms:(5R,15R)-5,6,14,15-tetrabenzyl-3,17-dioxa-6,14,23,24-tetraazatricyclo[17.3.1.1(8,12)]tetracosa-1⁽²³⁾,8,10,12⁽²⁴⁾,19,21-hexaene

Chemical Property of (5R,15R)-5,6,14,15-tetrabenzyl-3,17-dioxa-6,14,23,24-tetraazatricyclo[17.3.1.1(8,12)]tetracosa-1⁽²³⁾,8,10,12⁽²⁴⁾,19,21-hexaene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,15R)-5,6,14,15-tetrabenzyl-3,17-dioxa-6,14,23,24-tetraazatricyclo[17.3.1.1(8,12)]tetracosa-1⁽²³⁾,8,10,12⁽²⁴⁾,19,21-hexaene

There total 5 articles about (5R,15R)-5,6,14,15-tetrabenzyl-3,17-dioxa-6,14,23,24-tetraazatricyclo[17.3.1.1(8,12)]tetracosa-1⁽²³⁾,8,10,12⁽²⁴⁾,19,21-hexaene 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: 46.0%

2,6-bis-(bromomethyl)pyridine (7703-74-4) + (2R)-2-{benzyl[(6-{[benzyl-(2R)-(1-hydroxy-3-phenylpropan-2-yl)amino]methyl}pyridin-2-yl)methyl]amino}-3-phenylpropan-1-ol (1329682-32-7) → (5R,15R)-5,6,14,15-tetrabenzyl-3,17-dioxa-6,14,23,24-tetraazatricyclo[17.3.1.1(8,12)]tetracosa-1(23),8,10,12(24),19,21-hexaene (1329682-36-1)

Guidance literature:

(2R)-2-{benzyl[(6-{[benzyl-(2R)-(1-hydroxy-3-phenylpropan-2-yl)amino]methyl}pyridin-2-yl)methyl]amino}-3-phenylpropan-1-ol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 3h; Reflux; Inert atmosphere;

2,6-bis-(bromomethyl)pyridine; In tetrahydrofuran; at 0 ℃; for 59h; Reflux; Inert atmosphere;

DOI:10.1016/j.tet.2011.06.064

Reference yield:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → (5R,15R)-5,6,14,15-tetrabenzyl-3,17-dioxa-6,14,23,24-tetraazatricyclo[17.3.1.1(8,12)]tetracosa-1(23),8,10,12(24),19,21-hexaene (1329682-36-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate; iodine / tetrahydrofuran / Inert atmosphere

2.1: methanol / Reflux; Inert atmosphere

3.1: sodium tetrahydroborate / methanol / Inert atmosphere

4.1: sodium carbonate; potassium iodide / ethanol / 12 h / 100 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran / 3 h / 0 °C / Reflux; Inert atmosphere

5.2: 59 h / 0 °C / Reflux; Inert atmosphere

With sodium tetrahydroborate; iodine; sodium hydride; sodium carbonate; potassium iodide; In tetrahydrofuran; methanol; ethanol;

DOI:10.1016/j.tet.2011.06.064

Reference yield:

(R)-2-amino-3-phenylpropanol (5267-64-1) → (5R,15R)-5,6,14,15-tetrabenzyl-3,17-dioxa-6,14,23,24-tetraazatricyclo[17.3.1.1(8,12)]tetracosa-1(23),8,10,12(24),19,21-hexaene (1329682-36-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: methanol / Reflux; Inert atmosphere

2.1: sodium tetrahydroborate / methanol / Inert atmosphere

3.1: sodium carbonate; potassium iodide / ethanol / 12 h / 100 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran / 3 h / 0 °C / Reflux; Inert atmosphere

4.2: 59 h / 0 °C / Reflux; Inert atmosphere

With sodium tetrahydroborate; sodium hydride; sodium carbonate; potassium iodide; In tetrahydrofuran; methanol; ethanol;

DOI:10.1016/j.tet.2011.06.064

upstream raw materials:

2,6-bis-(bromomethyl)pyridine

(2R)-2-{benzyl[(6-{[benzyl-(2R)-(1-hydroxy-3-phenylpropan-2-yl)amino]methyl}pyridin-2-yl)methyl]amino}-3-phenylpropan-1-ol

(R)-2-amino-3-phenylpropanol

D-(R)-phenylalanine