(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-(phenoxymethyl)imidazo[1,2-a]pyridine

Base Information

• Chemical Name: (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-(phenoxymethyl)imidazo[1,2-a]pyridine
• CAS No.: 872581-18-5
• Molecular Formula: C₄₃H₄₂N₂O₅
• Molecular Weight: 666.817

Synonyms:(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-(phenoxymethyl)imidazo[1,2-a]pyridine

Chemical Property of (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-(phenoxymethyl)imidazo[1,2-a]pyridine

Chemical Property:

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Technology Process of (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-(phenoxymethyl)imidazo[1,2-a]pyridine

There total 2 articles about (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-(phenoxymethyl)imidazo[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: 77.0%

(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(chloromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (872581-16-3) + phenol (108-95-2,27073-41-2) → (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-(phenoxymethyl)imidazo[1,2-a]pyridine (872581-18-5)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 80 ℃; for 3.5h;

DOI:10.1002/hlca.200590199

Reference yield:

(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-methanol (263720-05-4) → (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-(phenoxymethyl)imidazo[1,2-a]pyridine (872581-18-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / SOCl₂ / CH₂Cl₂ / 0.42 h / 22 °C

2: 77 percent / t-BuOK / dimethylformamide / 3.5 h / 80 °C

With thionyl chloride; potassium tert-butylate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200590199

Reference yield: 63.0%

(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-(phenoxymethyl)imidazo[1,2-a]pyridine (872581-18-5) → (5R,6R,7S,8S)-5,6,7,8-tetrahydro-5-(hydroxymethyl)-2-(phenoxymethyl)imidazo[1,2-a]pyridine-6,7,8-triol

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; ethyl acetate; for 46h; under 760 Torr;

DOI:10.1002/hlca.200590199

upstream raw materials:

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

phenol

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

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