(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Base Information

• Chemical Name: (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine
• CAS No.: 1300698-50-3
• Molecular Formula: C₄₅H₄₂N₂O₄
• Molecular Weight: 674.839
• Mol file: 1300698-50-3.mol

Synonyms:(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Chemical Property of (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

There total 11 articles about (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 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: 69.0%

(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-iodo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (244138-64-5) + 4-n-methylphenylacetylene (766-97-2) → (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1300698-50-3)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.02.043

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1300698-50-3)

Guidance literature:

Multi-step reaction with 9 steps

1: ammonia / methanol / 2 h / 0 °C

2: acetic anhydride / dimethyl sulfoxide / 8 h / 20 °C / Inert atmosphere

3: formic acid; sodium cyanoborohydride / acetonitrile / 2.5 h / Reflux

4: Lawessons reagent / toluene / 28 h / 25 °C

5: mercury(II) diacetate / tetrahydrofuran / 0.83 h / 0 °C

6: toluene-4-sulfonic acid / water; toluene / 18 h / 65 °C

7: N-iodo-succinimide / N,N-dimethyl-formamide / 6 h / 80 °C

8: ethylmagnesium bromide / tetrahydrofuran / 0.17 h / 0 °C

9: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere

With Lawessons reagent; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; ethylmagnesium bromide; mercury(II) diacetate; ammonia; acetic anhydride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 2: Swern oxidation / 9: Sonogashira coupling;

DOI:10.1016/j.bmc.2011.02.043

Reference yield:

2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1-[(2',2'-dimethoxyethyl)imino]-1,5-imino-D-glucitol (191863-31-7) → (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1300698-50-3)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / water; toluene / 18 h / 65 °C

2: N-iodo-succinimide / N,N-dimethyl-formamide / 6 h / 80 °C

3: ethylmagnesium bromide / tetrahydrofuran / 0.17 h / 0 °C

4: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere

With N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ethylmagnesium bromide; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; 4: Sonogashira coupling;

DOI:10.1016/j.bmc.2011.02.043

upstream raw materials:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1-[(2',2'-dimethoxyethyl)imino]-1,5-imino-D-glucitol

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one

Downstream raw materials:

(5R,6R,7S,8S)-5-(hydroxymethyl)-2-(4-methylphenethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol