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

Base Information

• Chemical Name: (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-phosphonic acid
• CAS No.: 244138-74-7
• Molecular Formula: C₃₆H₃₇N₂O₇P
• Molecular Weight: 640.673
• Mol file: 244138-74-7.mol

Synonyms:

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

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]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-phosphonic acid

There total 2 articles about (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-phosphonic acid 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:

diethyl (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-phosphonate (244138-65-6) → (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-phosphonic acid (244138-74-7)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at 25 ℃; for 16h;

DOI:10.1002/(SICI)1522-2675(19990804)82:8<1137::AID-HLCA1137>3.0.CO;2-N

Reference yield:

(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) → (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-phosphonic acid (244138-74-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / 1,2,2,6,6-pentamethylpiperidine / [Pd(PPh₃)4] / toluene / 19.5 h / 95 °C

2: 241 mg / Me₃SiBr / CH₂Cl₂ / 16 h / 25 °C

With 1,2,2,6,6-pentamethylpiperidine; trimethylsilyl bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; toluene; 1: Substitution / 2: Substitution;

DOI:10.1002/(SICI)1522-2675(19990804)82:8<1137::AID-HLCA1137>3.0.CO;2-N

upstream raw materials:

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

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