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

Base Information

• Chemical Name: (5R,6R,7S,8S)-5-(hydroxymethyl)-2-(4-methylphenethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol
• CAS No.: 1300698-42-3
• Molecular Formula: C₁₇H₂₂N₂O₄
• Molecular Weight: 318.373
• Mol file: 1300698-42-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (5R,6R,7S,8S)-5-(hydroxymethyl)-2-(4-methylphenethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol 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: 71.0%

(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) → (5R,6R,7S,8S)-5-(hydroxymethyl)-2-(4-methylphenethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol (1300698-42-3)

Guidance literature:

With palladium on carbon; hydrogen; acetic acid; In methanol; water; ethyl acetate; at 20 ℃; for 56h; under 4500.45 Torr;

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)-5-(hydroxymethyl)-2-(4-methylphenethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol (1300698-42-3)

Guidance literature:

Multi-step reaction with 10 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

10: palladium on carbon; hydrogen; acetic acid / methanol; water; ethyl acetate / 56 h / 20 °C / 4500.45 Torr

With Lawessons reagent; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; palladium on carbon; ethylmagnesium bromide; mercury(II) diacetate; ammonia; hydrogen; acetic anhydride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; ethyl acetate; 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)-5-(hydroxymethyl)-2-(4-methylphenethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol (1300698-42-3)

Guidance literature:

Multi-step reaction with 5 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

5: palladium on carbon; hydrogen; acetic acid / methanol; water; ethyl acetate / 56 h / 20 °C / 4500.45 Torr

With N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium on carbon; ethylmagnesium bromide; hydrogen; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; methanol; water; ethyl acetate; 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

(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

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